Title: Book the Best Hotels with POOL in Chestertown in 2026 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Chestertown, MD from CA $122 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chestertown Hotels with a Pool Tonight [Jan 10 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-10&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-11&endDate=2026-01-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels with a pool ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/14760de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (865 reviews) "Everything was well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ahmed CA $141 CA $157 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.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) ### First Floor Studio Apartment in Historic Chestertown [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) Chestertown 9.6/10 Exceptional (108 reviews) "We had a lovely visit. It was nice and quiet and parking was perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne D. CA $137 CA $220 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/791afcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fd2dd5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) Middletown 9.2/10 Wonderful (333 reviews) "Clean room, great staff, recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $150 CA $166 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/3633d98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a7c447e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/d850b13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/678460fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) Aberdeen 9.0/10 Wonderful (1,001 reviews) "Room was great and staff excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $119 CA $133 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/18e3859d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/1c5b9984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/fafda427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/a5dd00be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) Aberdeen 8.6/10 Excellent (635 reviews) "High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $109 CA $122 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/e3d913c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/1feae509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/b95d3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown by IHG [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) Middletown 9.2/10 Wonderful (653 reviews) "Room was great the staff is so friendly every visit !!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis CA $125 CA $139 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/7e87d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) Middletown 8.8/10 Excellent (870 reviews) "Amazing stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katiana CA $132 CA $146 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/164fd394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/6f728b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Baltimore/Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) Aberdeen 9.0/10 Wonderful (609 reviews) "Excellent customer service at the front desk " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $117 CA $131 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/191cf636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/355fffa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/3bc97cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/d2d73c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Aberdeen-Bel Air by IHG [](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) Bel Air 8.0/10 Very good (478 reviews) "The staff is great, roon clean & spacious" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $115 CA $129 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/cbbf2396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (130 reviews) "Beautiful and peaceful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $176 CA $244 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.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.ca/Hotel-Search?startDate=2026-01-24&endDate=2026-01-25®ionId=7215&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Everything was clea" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "NA" [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Spotless hotel, staff was beyond incredible. They have won a customer for llife" [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "Delicious breakfast and very spacious rooms. " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Front desk staff and breakfast staff" [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "The hotel was beautiful, and the staff was courteous and friendly. " [](https://expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "All was well" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 10/10 Excellent "The staff was very courteous, the rooms are comfortable, all appliances and kitchenware were in working condition. The rooms were clean. An extended thank you to Ahmed for his professional service and hospitality. We will definitely return." [](https://expedia.ca/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Breakfast could have been better. Would have been nice to have fresher options. The suite was great, except one remote wasn’t working." [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chestertown? ### What is there to see and do in Chestertown? ### When is the best time to book a hotel with a pool in Chestertown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Belcamp ](https://www.expedia.ca/Belcamp-Hotels-Cheap-Hotels.0-0-d602125-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Belcamp ](https://www.expedia.ca/Belcamp-Hotels-Family-Hotel.0-0-d602125-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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