Title: Visit Chester: 2026 Travel Guide for Chester, Maryland | Expedia.com [Hotels in Chester](https://expedia.com/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d3000440455.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d3000440455.Destination-Travel-Guides) # Chester, MD ## Travel Guide ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Chester Things to do ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_3000440455) - Chester Hotel Deals - Vacation Rentals in Chester ![Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/409af264_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! Chester MD Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ... 10/10 Exceptional! (126 reviews) Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.. Reviewed on Sep 14, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F13%2F2026&endDate=3%2F14%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.com/Hotel-Search?startDate=3%2F13%2F2026&endDate=3%2F14%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD Fully refundableReserve now, pay when you stay $208 nightly $237 total Mar 6 - Mar 7 Total with taxes and fees Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ... 9/10 Wonderful! (1,877 reviews) Such a cool place to stay! Water pressure wasn’t great but it’s a very old building. Reviewed on Feb 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F6%2F2026&endDate=3%2F7%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court Annapolis MD $84 nightly $96 total Mar 3 - Mar 4 Total with taxes and fees Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ... 8.6/10 Excellent! (1,004 reviews) Staff Reviewed on Feb 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true®ionId=3000440455) [See all 1,177 properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F28%2F2026&endDate=3%2F1%2F2026®ionId=3000440455) 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. ![Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/409af264_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! Chester MD Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ... 10/10 Exceptional! (126 reviews) Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.. Reviewed on Sep 14, 2025 [](https://expedia.com/Chester-Hotels-Waterfront-Home-On-3-Acres-Fish.h33554342.Hotel-Information) ![Waterfront Sunset Bayview: sleeps 6](https://images.trvl-media.com/lodging/102000000/101620000/101618300/101618207/5ecd5370_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Sunset Bayview: sleeps 6 Chester MD Stay at this vacation home in Chester. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Bodkin Island and Chesapeake Bay Environmental ... [](https://expedia.com/Chester-Hotels-Waterfront-Sunset-Bayview-Sleeps-6.h101618207.Hotel-Information) ![Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac](https://images.trvl-media.com/lodging/23000000/22520000/22517000/22516965/e2c769bd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac Easton MD Stay at this vacation home in Easton. Enjoy free WiFi, private pools, and a sauna. Popular attractions Pickering Creek Audubon Center and Hog Neck Golf Course ... 10/10 Exceptional! (98 reviews) The host was lovely. Very responsive, thoughtful and welcoming!The home was perfect for our get away. It was better than the photos, comfy with a well appointed kitchen! Reviewed on Jan 3, 2026 [](https://expedia.com/Easton-Hotels-Beautiful.h22516965.Hotel-Information) [See all properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=3000440455&sort=VACATION_RENTAL) 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. ## Check Chester hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-27&endDate=2026-02-28)[Feb 27 - Feb 28](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-27&endDate=2026-02-28) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-28&endDate=2026-03-01)[Feb 28 - Mar 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-28&endDate=2026-03-01) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2%2F27%2F2026&endDate=3%2F1%2F2026)[Feb 27 - Mar 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2%2F27%2F2026&endDate=3%2F1%2F2026) ### Popular places to visit #### Chesapeake Exploration Center Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants. [](https://expedia.com/Chesapeake-Exploration-Center-Chester.d553248621561879491.Vacation-Attraction) ## Cities near Chester ![Aerial view of Kent Narrows peninsula inlet on Chesapeake in Grasonville Maryland, beach houses with private long docks for the sailboats line a road curving like an S shape with blue sky and water](https://images.trvl-media.com/place/7382/28b5ecb9-23b7-4e34-a5b1-5f438db18aae.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Grasonville ![Matapeake Fishing pier on the Chesapeake Bay in,Stevensville, Queen Anne's County, Maryland](https://images.trvl-media.com/place/162393/e2849665-7511-4327-9b6f-d13d77e9df34.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Stevensville ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Stevensville Hotels ](https://www.expedia.com/Stevensville-Hotels.d162393.Travel-Guide-Hotels) - [Hotel Wedding Venues Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Wedding-Hotels.0-0-d162393-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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[Chesapeake Bay Bridge ](https://www.expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) - [Car rentals near Stevensville ](https://www.expedia.com/Car-Rentals-In-Stevensville.d162393.Car-Rental-Guide) - [Enterprise Rental Cars in Stevensville ](https://www.expedia.com/Enterprise-Car-Rentals-In-Stevensville.d162393-c15.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Stevensville ](https://www.expedia.com/Avis-Car-Rentals-In-Stevensville.d162393-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Kent Narrows ](https://www.expedia.com/Car-Rentals-In-Kent-Narrows.d553248635077720315.Car-Rental-Guide) - [Hertz Rental Cars in Kent Island ](https://www.expedia.com/Hertz-Car-Rentals-In-Kent-Island.d553248635077608788-c40.Car-Rental-Guide-Suppliers) - [Car rentals near Northern Chesapeake Bay ](https://www.expedia.com/Car-Rentals-In-Northern-Chesapeake-Bay.d6051456.Car-Rental-Guide) - [Car rentals near Grasonville ](https://www.expedia.com/Car-Rentals-In-Grasonville.d7382.Car-Rental-Guide) - [Stevensville Vacation Rentals ](https://www.expedia.com/Stevensville-Vacation-Rentals.d162393.Travel-Guide-VacationRentals) - [Kent Island Vacation Rentals ](https://www.expedia.com/Kent-Island-Vacation-Rentals.d553248635077608788.Travel-Guide-VacationRentals) - [Grasonville Vacation Rentals ](https://www.expedia.com/Grasonville-Vacation-Rentals.d7382.Travel-Guide-VacationRentals) - [Things to do in Northern Chesapeake Bay ](https://www.expedia.com/Things-To-Do-In-Northern-Chesapeake-Bay.d6051456.Travel-Guide-Activities) - Cities near Chester - Places of interest [Grasonville](https://expedia.com/Grasonville.dx7382)[Stevensville](https://expedia.com/Stevensville.dx162393) - [Chesapeake Exploration Center ](https://expedia.com/Chesapeake-Exploration-Center-Chester.d553248621561879491.Vacation-Attraction) - [U.S. Naval Academy ](https://expedia.com/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction) - [Chesapeake Bay Bridge ](https://expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) - [Chesapeake Bay ](https://expedia.com/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Sandy Point State Park ](https://expedia.com/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction) - [Annapolis City Dock ](https://expedia.com/Annapolis-City-Dock-Historic-District.d553248633992240262.Vacation-Attraction) - [Anne Arundel Medical Center ](https://expedia.com/Anne-Arundel-Medical-Center-Annapolis.d553248621580159030.Vacation-Attraction) - [Maryland State House ](https://expedia.com/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction) - [Navy-Marine Corps Memorial Stadium ](https://expedia.com/Navy-Marine-Corps-Memorial-Stadium-Annapolis.d6091645.Vacation-Attraction) - [Westfield Annapolis Mall ](https://expedia.com/Westfield-Annapolis-Mall-Annapolis.d6172637.Vacation-Attraction) - [Chesapeake Bay Maritime Museum ](https://expedia.com/Chesapeake-Bay-Maritime-Museum-Downtown-St-Michaels.d553248633992441010.Vacation-Attraction) - [Annapolis Maritime Museum ](https://expedia.com/Annapolis-Maritime-Museum-Eastport.d553248621532662325.Vacation-Attraction) - [St. Michaels Winery ](https://expedia.com/St-Michaels-Winery-Downtown-St-Michaels.d553248633992438808.Vacation-Attraction) - [Annapolis Harbor Center Shopping Center ](https://expedia.com/Annapolis-Harbor-Center-Shopping-Center-Annapolis.d553248621563220686.Vacation-Attraction) - [Maryland Quiet Waters Park ](https://expedia.com/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) - [Chesapeake Bay Environmental Center ](https://expedia.com/Chesapeake-Bay-Environmental-Center-Grasonville.d553248621561196328.Vacation-Attraction) - [William Paca House ](https://expedia.com/William-Paca-House-Historic-District.d6077398.Vacation-Attraction) - [Queenstown Premium Outlets ](https://expedia.com/Queenstown-Premium-Outlets-Queenstown.d553248621532662352.Vacation-Attraction) - [Queenstown Harbor Golf Club ](https://expedia.com/Queenstown-Harbor-Golf-Club-Queenstown.d6091731.Vacation-Attraction) - [Maryland Hall for Creative Arts ](https://expedia.com/Maryland-Hall-For-Creative-Arts-Annapolis.d553248621580159031.Vacation-Attraction) - [Annapolis Mall Shopping Center ](https://expedia.com/Annapolis-Mall-Shopping-Center-Annapolis.d553248621563220690.Vacation-Attraction) - [Rock Hall Harbor ](https://expedia.com/Rock-Hall-Harbor-Rock-Hall.d553248621561173703.Vacation-Attraction) - [Avalon Theatre ](https://expedia.com/Avalon-Theatre-Easton.d6286426.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.com/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) - [Annapolis Harbour Center ](https://expedia.com/Annapolis-Harbour-Center-Edgewater.d553248621561879652.Vacation-Attraction) - [Hammond-Harwood House ](https://expedia.com/Hammond-Harwood-House-Historic-District.d6077396.Vacation-Attraction)