Title: The Best Chester Hotels with Pools from $90 - Hotels with indoor pools in Chester, MD | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx3000440455)[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) ![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=1200&h=500&q=medium) Photo by Patricia Knorr ![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### 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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Hotels with a Pool Tonight [Mar 14 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-03-14&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 15 - Mar 16](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-03-15&endDate=2026-03-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels with a pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/67743db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/86e1ff48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/e01c273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/d898936b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knapps Narrows Marina & Inn [](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) Sherwood 9.4/10 Exceptional (373 reviews) - Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures. $90 nightly $99 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/e0e2d461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/21c5252e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/4e51f020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn [](https://www.expedia.com/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) Easton 7.6/10 Good (848 reviews) - Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center. $82 nightly $90 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/bb752da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very Good (1,006 reviews) - Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary. $94 nightly $104 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/c52c5ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Corner (with Sofabed) | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/9187439c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/ec18bd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Easton Inn & Suites [](https://www.expedia.com/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) Easton 9.2/10 Wonderful (1,000 reviews) - Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round. $109 nightly $120 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/06cdc3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8d29fbd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8dfe0c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/814e7667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchored Inn at Hidden Harbour Marina [](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) Deale 9.4/10 Exceptional (478 reviews) - Pool paradise meets scenic marina views for a refreshing escape on the water. $169 nightly $193 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/97d2d16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (972 reviews) - Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers. $97 nightly $108 total Mar 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/bc6750c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/76eda657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/e9e3336f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds | Individually furnished, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5eb26742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn [](https://www.expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) St. Michaels 8.2/10 Very Good (1,001 reviews) - Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful. $98 nightly $108 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/7b97c3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville near Kent Island [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (880 reviews) - Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay. $93 nightly $104 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Indoor pool, open 5 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/w5755h3835x5y5-d8951a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/7fd1e967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/w5760h3835x0y5-ce75892e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/w5754h3835x5y5-441bbd30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina [](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1,002 reviews) - Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel. $114 nightly $127 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown [](https://www.expedia.com/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) Chestertown 9.6/10 Exceptional (108 reviews) - Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown. $144 nightly $159 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) 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://expedia.com/Hotel-Search?startDate=2026-03-28&endDate=2026-03-29®ionId=3000440455&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Chester Breakfast included 4 stars 5 stars Hot tub Spa ![](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=AFFINITY_SPRING_PROMO_3000440455) ## Top Chester Hotel Reviews ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg) ### Sonesta ES Suites Annapolis 8/10 Good "The room was spacious, clean but a little dated. The bathroom was small, haven’t seen a bathtub with curtain in a long time. My biggest peeve is how did they expect people to get to the hotel? There is a charge for parking a car. Not in a garage or covered garage port, but in an outdoor parking spot. Surely nobody is walking to this hotel. Another way o grab another dollar." [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "outstanding customer service and business support! give everyone a raise!!" [](https://expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent "Clean and spacious rooms " [](https://expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg) ### Crowne Plaza Annapolis by IHG 6/10 Okay "Room was clean" [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e_y.jpg) ### Hampton Inn & Suites Annapolis 8/10 Good "Only informed of charge for parking after arrival. " [](https://expedia.com/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg) ### Graduate by Hilton Annapolis 8/10 Good "Central l9cation, easy walk to all sites." [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ee980eab_y.jpg) ### St Michaels Inn 4/10 Poor "Continental breakfast was unavailable. When asked why breakfast was not available was told due to remodeling and that we should have been told when we checked in. Should have been informed long before check in! Bed was extremely uncomfortable, well past needing to be replaced." [](https://expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 6/10 Okay "Didn’t use anything. Ice machine was broken on our floor." [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Courtyard by Marriott Annapolis](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56_y.jpg) ### Courtyard by Marriott Annapolis 8/10 Good "The room was clean and well stocked with towels. I liked being able to walk outside to the patio. On addition, having a restaurantwith good food on-site is great!" [](https://expedia.com/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Chester? ### What is there to see and do in Chester? ### When is the best time to book a hotel with a pool in Chester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotel Wedding Venues Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Wedding-Hotels.0-0-d162393-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Romantic-Hotel.0-0-d162393-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Extended Stay Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Extended-Stay-Hotels.0-0-d162393-tExtendedStayHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stevensville ](https://www.expedia.com/Stevensville-Hotels-Historic-Hotel.0-0-d162393-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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