--- title: "Top 10 Hotels in Chester, MD (from $91) 2026 - Competitive Prices | Expedia" description: "Find 746 of the best hotels in Chester, MD in 2026. Most hotels are fully refundable." canonical: "https://www.expedia.com/Chester-Hotels.d3000440455.Travel-Guide-Hotels" language: en-US market: US currency: USD prices_as_of: 2026-11-14T21:03:01Z --- Plan your trip - [Chester Travel Guide](https://www.expedia.com/Chester.dx3000440455) - [Flights to Chester](https://www.expedia.com/Cheap-Flights-To-Chester.d3000440455.Travel-Guide-Flights) - [Things to do in Chester](https://www.expedia.com/Things-To-Do-In-Chester.d3000440455.Travel-Guide-Activities) - [Car Rentals in Chester](https://www.expedia.com/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide) - [Chester Vacation Packages](https://www.expedia.com/Chester.d3000440455.Destination-Travel-Guides) - [Vacation Rentals in Chester](https://www.expedia.com/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals) # Find hotels in Chester, MD from $91 ![A coastal town with a marina, a bridge, and a highway.](https://images.trvl-media.com/place/553248635976431770/56ba0bf4-a13e-43bd-887a-40cd11b0dfe0.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ### Upfront pricing Our total price for your stay includes taxes and fees ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Chester [Pet friendly](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&amenities=PETS) [Hot tub](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&amenities=HOT%5FTUB) [Pool](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&amenities=POOL) [Spa](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&amenities=SPA%5FON%5FSITE) [Family friendly](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&travelerType=family%5Ffriendly) [Apart­ment](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=APARTMENT) [Cottage](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=COTTAGE) [House­boat](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=HOUSE%5FBOAT) [Condo](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=CONDO) [Waterpark](https://www.expedia.com/Hotel-Search?destination=Chester,%20Maryland,%20United%20States%20of%20America®ionId=3000440455&latLong=38.975391,-76.289398&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&amenities=WATER%5FPARK) ## Check prices for these dates [Check prices for these dates, December 14 – 15, 2026](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-12-14&endDate=2026-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) [View in a map](https://www.expedia.com/Hotel-Search?regionId=3000440455&stayLength=1&daysInFuture=30&pwaOverlay=map) ## Our top choices for Chester hotels ### [1\. Lord Baltimore Hotel](https://www.expedia.com/Baltimore-Hotels-Lord-Baltimore-Hotel.h16091.Hotel-Information) ![A spacious dining area with multiple tables set for service, large windows, and a grand chandelier.](https://images.trvl-media.com/lodging/1000000/20000/16100/16091/d506e225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Downtown Baltimore - Guest rating: 8.4/10 (Very good, 3403 reviews) - Price: $104 nightly, $122 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Location, cleanliness and front desk staff Mr. He was very kind and helpful., by Valerie E., 13 days ago ### [2\. The Inn at Chesapeake Bay Beach Club](https://www.expedia.com/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b7ca7b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Stevensville - Guest rating: 9.4/10 (Exceptional, 514 reviews) - Price: $204 nightly, $226 total, Dec 9 - Dec 10, Total with taxes and fees - Review: The perfect getaway weekend with my husband! Will definitely go back., by Carolina, 4 days ago ### [3\. Kent Island Resort](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![A large, two-story barn-style building with a covered front porch and a garage.](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Stevensville - Guest rating: 9.2/10 (Wonderful, 190 reviews) - Price: $155 nightly, $169 total, Dec 1 - Dec 2, Total with taxes and fees - Review: Loved the property. Our room was beautiful., by Steven, September 22nd, 2026 ### [4\. La Quinta Inn & Suites by Wyndham Baltimore BWI Airport](https://www.expedia.com/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-BWI-Airport.h25898.Hotel-Information) ![A modern reception area with two counters, a cityscape mural, and recessed lighting.](https://images.trvl-media.com/lodging/1000000/30000/25900/25898/fba47221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Linthicum Heights - Guest rating: 8.4/10 (Very good, 4773 reviews) - Price: $72 nightly, $82 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Breakfast is your standard hotel breakfast. The staff were friendly., by Renee, 4 days ago ### [5\. Hyatt Place Kent Narrows & Marina](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Grasonville - Guest rating: 9.4/10 (Exceptional, 862 reviews) - Price: $134 nightly, $149 total, Nov 17 - Nov 18, Total with taxes and fees - Review: I enjoyed my stay for two nights. My room was clean., by Jean (Jeannie), 15 days ago ### [6\. Rod 'N' Reel Resort](https://www.expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Chesapeake Beach - Guest rating: 8.8/10 (Excellent, 1005 reviews) - Price: $165 nightly, $184 total, Dec 6 - Dec 7, Total with taxes and fees - Review: The front desk staff were nice. I truly enjoyed my stay at Rod N Reel., by Katesha, 2 days ago ### [7\. Hyatt Regency Baltimore Inner Harbor](https://www.expedia.com/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.Hotel-Information) ![An outdoor bar area with stone seating, umbrellas, and a view of a marina.](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/321aa461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Downtown West - Guest rating: 8.4/10 (Very good, 2066 reviews) - Price: $119 nightly, $140 total, Dec 7 - Dec 8, Total with taxes and fees - Review: Everything else about the hotel was very nice. The food at the restaurant was delicious., by Autumn, 3 days ago ### [8\. Hilton Garden Inn Kent Island Marina](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![A covered outdoor area with white wicker furniture and a view of boats in the background.](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/88ac4523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Grasonville - Guest rating: 8.8/10 (Excellent, 1001 reviews) - Price: $122 nightly, $136 total, Nov 22 - Nov 23, Total with taxes and fees - Review: The property was perfect. It was in walking distance to food., by Kauri, 8 days ago ### [9\. Holiday Inn Express Annapolis East-Kent Island by IHG](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Two Adirondack chairs facing a calm body of water with a clear sky above.](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Grasonville - Guest rating: 9.2/10 (Wonderful, 1002 reviews) - Price: $95 nightly, $105 total, Dec 13 - Dec 14, Total with taxes and fees - Review: Kindly welcomed at the front desk informed of all the amenities., by Shirley, 9 days ago ### [10\. The Royal Sonesta Harbor Court Baltimore](https://www.expedia.com/Baltimore-Hotels-Royal-Sonesta-Harbor-Court-Baltimore.h24651.Hotel-Information) ![A waterfront hotel with multiple floors, a marina with boats, and a cityscape in the background.](https://images.trvl-media.com/lodging/1000000/30000/24700/24651/0ce19377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Otterbein - Guest rating: 8.8/10 (Excellent, 2083 reviews) - Price: $144 nightly, $169 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Beautiful room, nice staff, good parking! I already am planning another stay., by John, 3 days ago ### [11\. Historic Inns of Annapolis](https://www.expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Historic District - Guest rating: 9/10 (Wonderful, 2072 reviews) - Price: $105 nightly, $120 total, Dec 3 - Dec 4, Total with taxes and fees - Review: We liked the location of inn which was near Main St and the dock area., by Bob, 4 days ago ### [12\. Renaissance Baltimore Harborplace Hotel](https://www.expedia.com/Baltimore-Hotels-Renaissance-Baltimore-Harborplace-Hotel.h9973.Hotel-Information) ![A modern lounge area with a sofa, ottomans, and a patterned wall.](https://images.trvl-media.com/lodging/1000000/10000/10000/9973/289a616e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Inner Harbor - Guest rating: 8.4/10 (Very good, 2513 reviews) - Price: $143 nightly, $168 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Room was nice. The front staff were great., by Johnny, 4 days ago ### [13\. Best Western Kent Narrows Inn](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![A multi-story hotel with a covered entrance and a flagpole.](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/w5755h3835x5y5-4fe9aeba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Grasonville - Guest rating: 8/10 (Very good, 1002 reviews) - Price: $90 nightly, $100 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Hot breakfast buffet was okay. Best Western website say 30 per pet stay., by Lauren, 13 days ago ### [14\. Pier 5 Hotel Baltimore](https://www.expedia.com/Baltimore-Hotels-Pier-5-Hotel-Baltimore.h28608.Hotel-Information) ![A spacious hotel lobby with multiple seating areas, a central staircase, and a large open space with a view of the lobby.](https://images.trvl-media.com/lodging/1000000/30000/28700/28608/c424948f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Inner Harbor - Guest rating: 8.2/10 (Very good, 1635 reviews) - Price: $92 nightly, $108 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Wonderful staff super nice. Overall nice hotel with a great location., by Michael, 3 days ago ### [15\. Hyatt Place Baltimore Inner Harbor](https://www.expedia.com/Baltimore-Hotels-Hyatt-Place-Baltimore-Inner-Harbor.h8842065.Hotel-Information) ![A city skyline with modern buildings, a marina with boats, and a well-lit waterfront area.](https://images.trvl-media.com/lodging/9000000/8850000/8842100/8842065/2c868f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Harbor East - Guest rating: 8.4/10 (Very good, 2674 reviews) - Price: $111 nightly, $131 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Location was great to walk all around!, by Steve, 4 days ago ### [16\. Quality Inn Grasonville near Kent Island](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![A spacious lobby with a staircase, a reception desk, and a dining area.](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Grasonville - Guest rating: 7.8/10 (Good, 1004 reviews) - Price: $82 nightly, $91 total, Dec 13 - Dec 14, Total with taxes and fees - Review: The staff was very friendly and helpful., by Marcia, 5 days ago ### [17\. Aloft by Marriott BWI Baltimore Washington International Airport](https://www.expedia.com/Baltimore-Hotels-Aloft-BWI-Baltimore-Washington-International-Airport.h2804098.Hotel-Information) ![A modern bar area with a patterned sofa, bar stools, and a variety of bottles on shelves.](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/da23316b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Linthicum Heights - Guest rating: 8.2/10 (Very good, 2004 reviews) - Price: $81 nightly, $92 total, Nov 22 - Nov 23, Total with taxes and fees - Review: Hotel was clean. The staff friendly Great view from our window of the planes landing., by liane, 7 days ago ### [18\. Live! Casino & Hotel Maryland](https://www.expedia.com/Baltimore-Hotels-Live-Casino-Hotel-BaltimoreWashington-BWI-Airport.h22837995.Hotel-Information) ![A spacious hotel lobby with a geometric patterned floor, a central reception desk, and a modern chandelier.](https://images.trvl-media.com/lodging/23000000/22840000/22838000/22837995/9458204c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Arundel Mills - Guest rating: 9.2/10 (Wonderful, 1009 reviews) - Price: $160 nightly, $183 total, Nov 23 - Nov 24, Total with taxes and fees - Review: Property is well maintained. Rooms are large. Attached to a large mall., by TsDiquah, 5 days ago ### [19\. Hilton Baltimore Inner Harbor](https://www.expedia.com/Baltimore-Hotels-Hilton-Baltimore-Inner-Harbor.h2027060.Hotel-Information) ![A long, dark wooden table with various decorative items and a bird sculpture, set against a large window with a city view.](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027060/3026c10e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Downtown West - Guest rating: 8.6/10 (Excellent, 1004 reviews) - Price: $152 nightly, $178 total, Nov 26 - Nov 27, Total with taxes and fees - Review: Room was clean. Staff were great!, by Chanel, 22 days ago ### [20\. Hotel Indigo Baltimore Downtown by IHG](https://www.expedia.com/Baltimore-Hotels-Hotel-Indigo-Baltimore-Downtown.h10902.Hotel-Information) ![A multi-story hotel with a classic architectural style, featuring arched windows and decorative trim.](https://images.trvl-media.com/lodging/1000000/20000/11000/10902/2c8fe3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Mount Vernon - Guest rating: 9.2/10 (Wonderful, 1142 reviews) - Price: $103 nightly, $121 total, Dec 14 - Dec 15, Total with taxes and fees - Review: Staff very helpful. They had a microwave delivered to the room., by Christina, 7 days ago Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=3000440455&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Compare top hotels in Chester | ![A spacious dining area with multiple tables set for service, large windows, and a grand chandelier.](https://images.trvl-media.com/lodging/1000000/20000/16100/16091/d506e225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)[Lord Baltimore Hotel](https://www.expedia.com/Hotel-Search?startDate=2026-11-22&endDate=2026-11-23&selected=16091&PinnedHotelID=16091&HadPinnedHotel=true®ionId=3000440455&adults=2&openPlayBack=true) Downtown Baltimore View | ![A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b7ca7b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)[The Inn at Chesapeake Bay Beach Club](https://www.expedia.com/Hotel-Search?startDate=2026-12-09&endDate=2026-12-10&selected=12402244&PinnedHotelID=12402244&HadPinnedHotel=true®ionId=3000440455&adults=2&openPlayBack=true) Stevensville View | ![A large, two-story barn-style building with a covered front porch and a garage.](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)[Kent Island Resort](https://www.expedia.com/Hotel-Search?startDate=2026-12-01&endDate=2026-12-02&selected=194102&PinnedHotelID=194102&HadPinnedHotel=true®ionId=3000440455&adults=2&openPlayBack=true) Stevensville View | ![A modern reception area with two counters, a cityscape mural, and recessed lighting.](https://images.trvl-media.com/lodging/1000000/30000/25900/25898/fba47221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)[La Quinta Inn & Suites by Wyndham Baltimore BWI Airport](https://www.expedia.com/Hotel-Search?startDate=2026-11-22&endDate=2026-11-23&selected=25898&PinnedHotelID=25898&HadPinnedHotel=true®ionId=3000440455&adults=2&openPlayBack=true) Linthicum Heights View | ![A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)[Hyatt Place Kent Narrows & Marina](https://www.expedia.com/Hotel-Search?startDate=2026-11-17&endDate=2026-11-18&selected=77974873&PinnedHotelID=77974873&HadPinnedHotel=true®ionId=3000440455&adults=2&openPlayBack=true) Grasonville View | | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | 8.4Very good3,403 reviews | 9.4Exceptional514 reviews | 9.2Wonderful190 reviews | 8.4Very good4,773 reviews | 9.4Exceptional862 reviews | | $104 nightly $122 total Nov 22 - Nov 23Total with taxes and fees | $204 nightly $226 total Dec 9 - Dec 10Total with taxes and fees | $155 nightly $169 total Dec 1 - Dec 2Total with taxes and fees | $72 nightly $82 total Nov 22 - Nov 23Total with taxes and fees | $134 nightly $149 total Nov 17 - Nov 18Total with taxes and fees | | Breakfast includedPoolSpaPet friendlyWiFi includedParking | Breakfast includedPoolSpaPet friendlyWiFi includedParking | Breakfast includedPoolSpaPet friendlyWiFi includedParking | Breakfast includedPoolSpaPet friendlyWiFi includedParking | Breakfast includedPoolSpaPet friendlyWiFi includedParking | ## Where to stay near Chester Chester, MD, offers a delightful blend of outdoor adventures and scenic beauty. Explore featured destinations along the Eastern Shore, enjoy stunning water views, and stroll down High Street. Whether you seek family-friendly activities or a relaxing atmosphere, Chester is a perfect getaway for any traveler. - [Stevensville](#) - [Annapolis](#) - [Kent Narrows](#) - [Kent Island](#) - [Grasonville](#) ![A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.](https://images.trvl-media.com/place/162393/e2849665-7511-4327-9b6f-d13d77e9df34.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Jennifer Crim [View properties in map for Stevensville](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=162393) ### Stevensville Discover Stevensville, a welcoming destination perfectly suited for travelers seeking a blend of business, family, and outdoor experiences. This charming city offers easy access to attractions like the Chesapeake Bay Bridge and Sandy Point State Park, where you can enjoy scenic views and beach activities. With its proximity to Chester, just about a mile away by car, Stevensville is a smart choice for your stay, providing a great base for a memorable getaway. [See properties](https://www.expedia.com/Hotel-Search?regionId=162393) ![A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.](https://images.trvl-media.com/place/6034082/a3002046-1aee-4bd3-be34-8475c830687e.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Annapolis](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6034082) ### Annapolis Experience the charm of Annapolis, a delightful hub for family travelers and weekend getaways who want to explore its rich history and stunning waterfront. With attractions like the Chesapeake Bay Bridge, Sandy Point State Park, and the Annapolis Maritime Museum, visitors can enjoy a mix of outdoor activities and cultural experiences. Located about 18 miles by car from Chester, Annapolis offers easy access to a vibrant atmosphere, making it a smart choice for your stay. [See properties](https://www.expedia.com/Hotel-Search?regionId=6034082) ![A marina with boats, a bridge, and houses along the water's edge.](https://images.trvl-media.com/place/553248635077720315/b3cb87d1-af24-4893-9b84-7feb8799af32.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Patricia Knorr [View properties in map for Kent Narrows](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635077720315) ### Kent Narrows If you are an outdoor enthusiast or a family traveler, look no further than Kent Narrows, known for its stunning Chesapeake Bay views and vibrant beach experiences. This charming village offers easy access to attractions like the Chesapeake Bay Environmental Center and Sandy Point State Park, perfect for enjoying the great outdoors. Located about 3 miles by car from Chester, Kent Narrows makes for a smart choice for your stay, combining relaxation with ample opportunities for adventure. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635077720315) ![A coastal town with a marina, a bridge, and a highway.](https://images.trvl-media.com/place/553248635976431770/56ba0bf4-a13e-43bd-887a-40cd11b0dfe0.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Patricia Knorr [View properties in map for Kent Island](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248635077608788) ### Kent Island Kent Island stands out as a prime spot for outdoor enthusiasts and families interested in a scenic getaway. With its beautiful beaches, stunning views of the Chesapeake Bay, and access to attractions like Sandy Point State Park and the Chesapeake Bay Bridge, visitors can enjoy a variety of activities year-round. Located about 3 miles from Chester, Kent Island offers a perfect blend of relaxation and adventure, making it a smart choice for your next vacation. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248635077608788) ![An aerial view of a coastal residential area with houses, docks, and a clear blue sky.](https://images.trvl-media.com/place/7382/28b5ecb9-23b7-4e34-a5b1-5f438db18aae.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Grasonville](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=7382) ### Grasonville Travelers visiting the area often choose Grasonville, especially those with an affinity for outdoor adventures and family-friendly experiences. This charming city offers easy access to the stunning Chesapeake Bay, the serene Eastern Neck National Wildlife Refuge, and the educational Chesapeake Bay Environmental Center. With its vibrant boardwalk and shopping options, Grasonville is a delightful base for exploring nearby Chester, located about 4 miles away. Enjoy a memorable stay in Grasonville, where diverse activities await you. [See properties](https://www.expedia.com/Hotel-Search?regionId=7382) ## Stay near popular Chester attractions Chester, Maryland, offers a perfect getaway for outdoor enthusiasts and families alike. With stunning parks, picturesque marinas, and beautiful beaches, there’s something for everyone. Explore the natural beauty and cultural experiences that make this charming destination a must-visit for your next vacation. ### Chesapeake Bay Bridge ![A large suspension bridge over a body of water with a sandy beach in the foreground.](https://images.trvl-media.com/place/6077400/ae959a88-8499-47be-a61a-71735853de7a.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 8.8/10 (1,066 reviews) Set the stage for your next adventure at the Chesapeake Bay Bridge, a stunning modern marvel that offers breathtaking views and a vibrant atmosphere. Located about 7 miles from Chester, this iconic bridge connects you to the best of Maryland's coastal charm, making it an ideal spot for your vacation exploration. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6077400) ### Sandy Point State Park ![A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.](https://images.trvl-media.com/place/6163398/64112244-6567-4808-b1e3-4cc8eb78360c.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 8.6/10 (221 reviews) Ideal for families and outdoor lovers, Sandy Point State Park offers a beautiful blend of adventure and scenery. With its extensive trails and waterfront views, visitors can enjoy a variety of recreational activities. Located about 7 miles from Chester, it's a convenient spot for a memorable day out in nature. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6163398) ### Maryland State House ![A town with historic buildings, a prominent church steeple, and a weather vane atop a building.](https://images.trvl-media.com/place/6077394/fad2b17b-4810-4b33-9426-2e543063ace6.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 9.0/10 (433 reviews) An iconic landmark that appeals to history buffs, the Maryland State House is a historic civic government building in Annapolis, showcasing rich culture and architecture. Located about 11 miles from Chester, it offers a unique glimpse into Maryland's past, making it a convenient spot for travelers eager to explore the area. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6077394) ### Maryland Quiet Waters Park ![A forest trail with a sign indicating boat and bike rentals, and park closure at dusk.](https://images.trvl-media.com/place/6172639/092975c5-56e1-4eba-b84e-d0c85edffb07.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 8.4/10 (49reviews) A must-see for families seeking outdoor fun, Maryland Quiet Waters Park offers scenic trails and serene nature spots perfect for relaxation. Located about 11 miles from Chester, this urban park provides a refreshing escape, making it a convenient choice for your getaway. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6172639) ### Sandy Point Beach Rating: 9.6/10 (10 reviews) This prominent local landmark is ideal for travelers interested in a relaxing beach experience. Sandy Point Beach offers inviting sandy shores and vibrant beach vibes, creating the perfect spot for sunbathing and picnicking. Located about 6 miles from Chester, it’s a convenient getaway for those staying nearby. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635983987021) ### Chesapeake Bay Environmental Center Rating: 8.6/10 (45 reviews) No trip is complete without a visit to the Chesapeake Bay Environmental Center, a haven for nature lovers and eco-conscious travelers. Here, you can immerse yourself in the beauty of the Chesapeake Bay while enjoying educational programs and outdoor activities. Located about 4 miles from Chester, it offers easy access to a unique natural experience. Staying nearby ensures you can explore the center’s offerings at your leisure. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561196328) ### Eastern Neck National Wildlife Refuge Rating: 9.8/10 (6 reviews) An essential stop for families seeking outdoor adventures, Eastern Neck National Wildlife Refuge offers a unique experience with its diverse wildlife and scenic views. Located about 5 miles from Chester, this budget-friendly destination allows visitors to immerse themselves in nature while enjoying the convenience of nearby accommodations. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635974660968) ### Annapolis Maritime Museum Rating: 9.0/10 (27 reviews) Enjoy the simplicity of a visit to the Annapolis Maritime Museum, perfect for culture lovers seeking to explore maritime history. This museum showcases the region's rich nautical heritage through engaging exhibits and programs. Located about 19 miles by car from Chester, it offers a convenient stop to enrich your Maryland adventure. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662325) ## Learn more about Chester Chester awaits: its island views, sunny weather, golf, and more! [See all hotels in Chester](https://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&adults=2®ionId=3000440455) ![A coastal town with a marina, a bridge, and a highway.](https://images.trvl-media.com/place/553248635976431770/56ba0bf4-a13e-43bd-887a-40cd11b0dfe0.jpg?impolicy=fcrop&w=900&h=338&p=1&q=high) ## Top Chester Hotel Reviews ### [Hyatt Place Kent Narrows & Marina](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3028 KENT NARROW WAY S, Grasonville, MD, 21638, US - Location: Grasonville - Star rating: 3/5 - Guest rating: 9.4/10 (862 reviews) - Review: Loved it, by Joe, May 6, 2025, rated 10/10 Excellent ### [Holiday Inn Express Annapolis East-Kent Island by IHG](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Two Adirondack chairs facing a calm body of water with a clear sky above.](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1020 Kent Narrows Rd, Grasonville, MD, 21638, US - Location: Grasonville - Star rating: 2.5/5 - Guest rating: 9.2/10 (1002 reviews) - Review: The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look..., by Christina, July 17, 2023, rated 10/10 Excellent ### [The Inn at Chesapeake Bay Beach Club](https://www.expedia.com/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b7ca7b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 180 Pier One Road, Stevensville, MD, 21666, US - Location: Stevensville - Star rating: 4/5 - Guest rating: 9.4/10 (514 reviews) - Review: Beautiful place, quiet and clean., by Chuck, May 15, 2025, rated 10/10 Excellent ### [Hilton Garden Inn Kent Island Marina](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![A covered outdoor area with white wicker furniture and a view of boats in the background.](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/88ac4523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3206 Main St, Grasonville, MD, 21638, US - Location: Grasonville - Star rating: 3/5 - Guest rating: 8.8/10 (1001 reviews) - Review: I had a very nice stay, the room had a very nice view of the Bay., by Kathie, January 17, 2017, rated 10/10 Excellent ### [Kent Island Resort](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![A large, two-story barn-style building with a covered front porch and a garage.](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 500 Kent Manor Dr, Stevensville, MD, 21666, US - Location: Stevensville - Star rating: 3.5/5 - Guest rating: 9.2/10 (190 reviews) - Review: I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay., by John, March 27, 2025, rated 10/10 Excellent ### [Historic Inns of Annapolis](https://www.expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 58 State Circle, Annapolis, MD, 21401, US - Location: Historic District - Star rating: 3.5/5 - Guest rating: 9/10 (2072 reviews) - Review: Lovely property in the heart of Annapolis. Quiet yet convenient to downtown. Connor was awesome! He took care of our every need., by Robert, February 19, 2024, rated 10/10 Excellent ### [Best Western Kent Narrows Inn](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![A multi-story hotel with a covered entrance and a flagpole.](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/w5755h3835x5y5-4fe9aeba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3101 Main Street, Grasonville, MD, 21638, US - Location: Grasonville - Star rating: 2.5/5 - Guest rating: 8/10 (1002 reviews) - Review: My family and I booked here on the 26th and have decided to stay for a few extra days. The staff are all amazing and very helpful. I have 2 service dogs so the hotel was very accommodating about it. Will definitely recommend this hotel to others., by Valerie, April 1, 2024, rated 10/10 Excellent ### [Inn at Huntingfield Creek](https://www.expedia.com/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) ![A boat deck with a white bench and a view of a calm lake and distant trees.](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Rock Hall - Review: Quaint property - very laid-back. Exactly what we were looking for., by George, February 28, 2023, rated 10/10 Excellent ### [Quality Inn Grasonville near Kent Island](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![A spacious lobby with a staircase, a reception desk, and a dining area.](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 101 Vfw Ave, Grasonville, MD, 21638, US - Location: Grasonville - Star rating: 2.5/5 - Guest rating: 7.8/10 (1004 reviews) - Review: My wife and have been staying here off and on for a few years now. We have always found it to a lovely place stay . The staff there is especially courteous and helpful whenever a special need arises ! We give special notice of thanks to general manager Amy Patel for her attention to service and her pleasant attitude at all times ! Her caring manner and attention to detail are par excellence ! The cleanliness , breakfast included , location and the inground pool make this a sure bet for any..., by Chuck, August 7, 2016, rated 10/10 Excellent ### [Hilton Garden Inn Annapolis Downtown](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/w5752h3837x5y3-99f5dc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: This is always a great stay. The location is really good, the staff is very friendly and professional, the bar is nice and the appetizers are delicious. My room is always spotless and the bath is spacious and bright!, by Robert, January 26, 2023, rated 10/10 Excellent ### [Country Inn & Suites by Radisson, Annapolis, MD](https://www.expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: The property is a great location. An easy drive to DTA and convenient to the mall and restaurants west of Annapolis., by Anonymous traveler, December 26, 2024, rated 10/10 Excellent ### [134 Prince - Luxury Boutique Hotel](https://www.expedia.com/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) ![A two-story white building with a central entrance, steps, and a pink door.](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/ee6098f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!, by Reyna, February 15, 2025, rated 10/10 Excellent ### [Fairfield Inn & Suites by Marriott Easton](https://www.expedia.com/Easton-Hotels-Fairfield-Inn-Suites-By-Marriott-Easton.h12009838.Hotel-Information) ![A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.](https://images.trvl-media.com/lodging/13000000/12010000/12009900/12009838/2322f180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Easton - Review: The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff..., by Richard, December 30, 2023, rated 10/10 Excellent ### [86 State Circle - Luxury Boutique Hotel](https://www.expedia.com/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![A church with a spire, surrounded by trees and illuminated by warm lights.](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/235d9b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Historic District - Review: The property was immaculate! The room we stayed (Chase suite) was gorgeous!! The staff were so wonderful and helpful and the location was perfect. Loved everything about this property, by MARA, October 31, 2026, rated 10/10 Excellent ### [Fairfield Inn & Suites By Marriott Annapolis](https://www.expedia.com/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) ![A modern living room with a fireplace, a sofa, and a coffee table.](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/w3996h2664x4y0-50b1ab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: Property opened 5/2024\. Still pristine when I visited with my fam. Free breakfast was very good. Gym is as you would expect in a Marriott- great. Staff working out some kinks in the check in process. Understandable to me as this is a new team. Nasty surprise when we checked in to learn there was a $30 parking fee. The lot is self park and an open lot. This was not disclosed when I booked on Expedia. I will not return to this property for this reason., by ronald, July 5, 2024, rated 10/10 Excellent ### [DoubleTree by Hilton Hotel Annapolis](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: Excellent and friendly service provided to hotel guests. From the front desk to restaurant, to housekeeping and also the Transport shuttle!, by Celina, May 27, 2025, rated 10/10 Excellent ### [Crowne Plaza Annapolis by IHG](https://www.expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/3e34bf99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: Clean, Comfortable, and great service., by John, June 14, 2023, rated 10/10 Excellent ### [SpringHill Suites by Marriott Annapolis](https://www.expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/72ca553e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Review: Perfect for what we needed, by Julie, April 1, 2025, rated 10/10 Excellent ## Find out more about Chester ### Top reasons to visit Chester - **Scenic Waterfront Strolls:** Enjoy relaxing walks along Chester's picturesque waterfront, perfect for soaking in the sun and beautiful views. - **Outdoor Recreation:** Explore urban parks and a marina, offering various activities for outdoor enthusiasts and families alike. - **Vibrant Downtown Area:** Discover charming shops and local dining options in Chester's lively downtown, ideal for a fun day out. - **Historic Atmosphere:** Experience the rich history of Chester through its historic houses and nearby cultural sites. - **Diverse Lodging Options:** Choose from pet-friendly hotels, cozy bed & breakfasts, and family-friendly accommodations for a comfortable stay. ### Find great hotels near Chester Experience the charm of Chester, Maryland, with a variety of lodging options tailored to every traveler. Whether you're seeking a pet-friendly hotel, a cozy bed & breakfast, or accommodations for a family vacation, Chester has you covered. Enjoy convenient access to essential amenities designed for business travelers and leisure seekers alike. Discover the best hotels in Chester that promise comfort and hospitality for a memorable stay. - **[Country Inn & Suites by Radisson, Annapolis, MD: ](https://www.expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)** Experience a warm and welcoming atmosphere at this 3-star hotel, rated 9.0 by guests. Located 14 miles from Chester, this property is ideal for travelers seeking a pet-friendly environment with business travel amenities. Enjoy spacious rooms equipped for relaxation and productivity. The hotel offers convenient features such as a dog exercise area and flexible pet policies, ensuring a comfortable stay for you and your furry companions. - **[Graduate by Hilton Annapolis: ](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)** With a guest rating of 9.4, this 4-star hotel offers a charming blend of family-friendly and business-oriented accommodations just 11 miles from Chester. The Graduate by Hilton embraces a collegiate theme, making it perfect for families and professionals alike. Enjoy amenities tailored for children, including free cribs, and take advantage of the welcoming pet policy. Guests appreciate the vibrant atmosphere and modern comforts this property provides, making it a great choice for all. - **[Historic Inns of Annapolis: ](https://www.expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)** Nestled in a national historic building, this 3.5-star hotel boasts a guest rating of 9.0 and is located 11 miles from Chester. Ideal for those seeking a unique adventure and family vacation, the Historic Inns of Annapolis offers exciting recreational activities nearby, such as kayaking and hiking. The hotel also caters to families with children-friendly amenities, ensuring a delightful stay for guests of all ages. Immerse yourself in the rich history and charm of this remarkable property. ### Where to stay near Chester Chester, Maryland, is a charming city perfect for outdoor enthusiasts and beach lovers. With its sunny weather and scenic views, visitors can enjoy relaxing strolls along the waterfront or explore the vibrant downtown area. Nearby, experience family-friendly neighborhoods with welcoming locals and a rich historical atmosphere. Whether you’re seeking adventure or a serene getaway, Chester promises a delightful vacation filled with charm and memorable moments. - **[Stevensville: ](https://www.expedia.com/Stevensville-Hotels.d162393.Travel-Guide-Hotels)** Nestled just a mile from Chester, Stevensville offers a charming blend of outdoor adventure and scenic beauty. With its peak visitor numbers in April and the summer months of June and July, this city is a popular destination for those seeking a beach experience. Enjoy the local recreational areas and picturesque boardwalks, perfect for leisurely strolls or picnics. The nearby Chesapeake Bay and state parks provide ample opportunities for exploration and relaxation, making Stevensville an ideal spot for nature lovers and families alike. - **[Annapolis: ](https://www.expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)** A mere 11 miles from Chester, Annapolis is a vibrant city known for its rich history and family-friendly atmosphere. With visitor numbers peaking in the summer months of July and August, this charming city offers a diverse range of experiences. Explore the historic academy, enjoy shopping at local centers, or take in the breathtaking views of the bay and beach. Whether you're interested in educational opportunities or simply soaking in the city's unique culture, Annapolis promises an engaging visit year-round. - **[Kent Narrows: ](https://www.expedia.com/Kent-Narrows-Hotels.d553248635077720315.Travel-Guide-Hotels)** Located just 3 miles from Chester, Kent Narrows is a quaint village that attracts visitors with its picturesque waterfront and family-oriented activities. The village experiences peak tourist arrivals during the summer months of June to August, making it a lively destination for beachgoers. With its inviting boardwalk and various shopping centers, Kent Narrows offers a delightful blend of leisure and recreation. The nearby esplanade and stunning views of the bay make it a perfect getaway for those looking to unwind and enjoy the natural surroundings. ### Things to do near Chester Chester, Maryland, offers a delightful escape for outdoor enthusiasts and beach lovers. Enjoy scenic strolls along the boardwalk, explore recreational areas, and take advantage of local attractions. Whether you're looking for a vibrant shopping experience or guided tours to discover the area's charm, Chester has something for everyone. Embrace the picturesque views and unique amenities that make this quaint town a perfect getaway. **Shopping** For unique gifts and souvenirs, explore local shops in Chester, like The Gifted Bird and Chester River Wine & Cheese. If you're up for a drive, head to the nearby Queenstown Premium Outlets for a wider selection of brands and deals, just a short distance away. **Recreation** Experience luxury at [Old South Country Club](https://www.expedia.com/Old-South-Country-Club-Hotels.0-l553248621532662175-0.Travel-Guide-Filter-Hotels), where you can enjoy golf amidst beautiful scenery. Indulge in the serene atmosphere, relax in the clubhouse, and savor fine dining options, all while embracing the peaceful surroundings that enhance your wellness journey. **Adventure** Explore the scenic Chester River by renting a kayak or paddleboard, enjoying the beautiful waterways and wildlife. For a thrilling experience, head to the nearby Chesapeake Bay for fishing or crabbing, soaking in the sun while engaging in these fun outdoor activities. **Nightlife** Explore the lively atmosphere at The Narrows Restaurant for waterfront dining and cocktails. For a more casual vibe, check out The Fisherman's Inn, where you can enjoy local seafood and live music. Don't miss the nearby craft breweries for a taste of local brews and a fun night out. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Booking tips and Expedia advantages for Chester - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chester is Monday. The most expensive day to stay in Chester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to tailor your options based on your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will show you sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package deal. ### Find the best attractions near Chester Chester, Maryland, is perfect for outdoor enthusiasts and beach lovers, featuring beautiful scenery and a variety of attractions. Visitors can explore urban parks, a marina, and historic houses, making it an ideal destination for culture-seekers and families alike. With plenty of options for outdoor activities and enriching experiences, Chester promises a memorable vacation for all who visit. - **[Chesapeake Bay Bridge: ](https://www.expedia.com/Chesapeake-Bay-Bridge-Hotels.0-l6077400-0.Travel-Guide-Filter-Hotels)** Experience the impressive engineering of this modern marvel, spanning over 4 miles. With stunning views of the Chesapeake Bay and the surrounding landscapes, this iconic bridge offers a unique perspective of the area and the bustling city vibes nearby. - **[Sandy Point State Park: ](https://www.expedia.com/Sandy-Point-State-Park-Hotels.0-l6163398-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the natural beauty of this national state park, featuring scenic trails and abundant wildlife. Perfect for adventure seekers, you can hike, bike, or picnic while enjoying the great outdoors and refreshing vibes. - **[Sandy Point Beach: ](https://www.expedia.com/Sandy-Point-Beach-Hotels.0-l553248635983987021-0.Travel-Guide-Filter-Hotels)** Relax and soak up the sun at this beautiful beach, known for its soft sands and inviting waters. It's an ideal spot for swimming, beach games, and enjoying the laid-back coastal atmosphere. ### Best time to go to Chester The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain. | **Calendar Month** | **Temperature** | **Precipitation** | **Cloudiness** | **Occupancy** | **Pricing** | | ------------------ | --------------- | ----------------- | -------------- | ------------- | ------------- | | January | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 37.4°F (3.0°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 43.9°F (6.6°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.1°F (12.3°C) | Light Rain | Mostly Sunny | Average | Average | | May | 63.5°F (17.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 77.9°F (25.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 76.3°F (24.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 70.5°F (21.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | October | 60.3°F (15.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 48.7°F (9.3°C) | Light Rain | Mostly Sunny | Average | Average | | December | 41.0°F (5.0°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Chester Traveling to Chester, Maryland, you have a few airport options. Philadelphia International Airport ([PHL](https://www.expedia.com/Philadelphia-Intl-Airport-Hotels.0-aPHL-0.Travel-Guide-Filter-Hotels)) is 84 miles away, with nearby hotels like [W Philadelphia](https://www.expedia.com/Philadelphia-Hotels-W-Philadelphia.h45967702.Hotel-Information) and The Rittenhouse, both 6 miles from the airport. Washington, D.C.'s Ronald Reagan Washington National Airport ([DCA](https://www.expedia.com/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)) is closer at 41 miles, offering luxury stays such as the InterContinental Washington D.C. - The Wharf and [Salamander Washington DC](https://www.expedia.com/Washington-Hotels-Salamander-Washington-DC.h1044257.Hotel-Information), both 2 miles away. Washington Dulles International Airport ([IAD](https://www.expedia.com/Washington-Dulles-Intl-Airport-Hotels.0-aIAD-0.Travel-Guide-Filter-Hotels)) is also accessible at 62 miles, with hotels like [The Westin Washington Dulles Airport](https://www.expedia.com/Herndon-Hotels-The-Westin-Washington-Dulles-Airport.h3014272.Hotel-Information) and [Washington Dulles Airport Marriott](https://www.expedia.com/Sterling-Hotels-Washington-Dulles-Airport-Marriott.h15635.Hotel-Information), just 1 mile and 0.4 miles away, respectively. Each hotel provides convenient transportation to its corresponding airport. ## Frequently Asked Questions ### What is the best area to stay in Chester? The best area to stay in Chester is along the Kent Narrows, which offers convenient water access and a variety of dining options. This area is the commercial hub of Chester, situated directly on the water where the Kent Narrows Bridge connects Kent Island to the mainland. You'll find a selection of hotels, waterfront restaurants, and marinas here. It's a practical base for exploring the Chesapeake Bay area. For couples looking for a relaxing getaway, staying near the Kent Narrows is ideal. Many hotels in this area offer views of the water, and you can easily enjoy a meal at a waterfront restaurant or take a stroll along the docks. The convenience of having dining and water activities within walking distance makes for a stress-free trip. Families will also find the Kent Narrows area suitable due to the range of dining choices and easy access to activities. Some hotels offer amenities like outdoor pools, and the proximity to the water provides opportunities for boat tours or fishing charters. ### When is the best time to go to Chester? The best time to go to Chester is during the shoulder seasons of spring (April-May) and fall (September-October) when the weather is pleasant and crowds are smaller. These months offer comfortable temperatures for exploring the outdoors and enjoying the Chesapeake Bay. You'll find fewer visitors compared to the peak summer months, making it easier to enjoy local attractions, dining, and scenic drives. Spring brings blooming flowers, while fall showcases colorful foliage, creating beautiful backdrops for your visit. For those looking to enjoy water activities, the summer months (June-August) are ideal. While it's the busiest time, the warm weather is superb for boating, fishing, and swimming. Many local events and outdoor festivals also take place during this period, offering a lively experience. ### Can I cancel my hotel reservation on Expedia? You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester. ### How much is the nightly rate at a Chester hotel? Prices for hotels in Chester often vary, but you can find a great deal from $91 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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