Title: Book the Best Hotels with POOL in Chestertown in 2025 | 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) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find Hotels with a Pool in Chestertown, MD from CA $133 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Edgewood/Aberdeen-South Edgewood 9.4/10 Exceptional (1002) "Very good breakfast options Convenient parking Clean room Friendly staff" CA $119 CA $133 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.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) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (903) "The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!" CA $177 CA $197 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/8c995ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/ffece2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/cfe3570f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express White Marsh by IHG Nottingham 9.6/10 Exceptional (943) "Staff was very nice and rooms were clean. Breakfast was great too!!" CA $149 CA $172 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/72a73d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing Chestertown 7.8/10 Good (70) "Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!" CA $185 CA $211 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.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) ![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) ### First Floor Studio Apartment in Historic Chestertown Chestertown 9.6/10 Exceptional (102) "A charming studio in a quiet neighborhood. great directions from host on how to use the property - " CA $138 CA $222 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/4dc8f4ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.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/da06d995.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) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (825) "Friendly staff, clean room, convenient location. " CA $160 CA $177 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.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) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.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) ### Fairfield Inn & Suites by Marriott Middletown Middletown 9.2/10 Wonderful (289) "Friendly staff, comfortable bed and clean room " CA $141 CA $156 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/128f221c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/0669e46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3cc8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/dc410dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown by IHG Middletown 9.2/10 Wonderful (625) "Check in staff was awesome!" CA $162 CA $180 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/3f583294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/c423f238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/c4d91e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/10000000/9340000/9330600/9330578/149f435b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mariners Motel Rock Hall 9.4/10 Exceptional (90) "Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. " CA $201 CA $223 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Rock-Hall-Hotels-Mariners-Motel.h9330578.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/72010305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/f2afc3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Zen Cottage | Living area](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/7be1e889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/8889a53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Huntingfield Creek Rock Hall 10/10 Exceptional (53) "Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. " CA $195 CA $217 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.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=2025-10-19&endDate=2025-10-20®ionId=7215&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Sagamore Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Sagamore Pendry Baltimore 10/10 Excellent "Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!" [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](//images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "Very nice staff" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Easy access, dmooth check in, felt safe parking, close to port. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](//images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Clean and spacious room with great amenities " [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Nice hotel" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Aberdeen-APG](//images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3_y.jpg) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG 10/10 Excellent "Absolutely a go to for booking family when in town. Great staff. Clean, good breakfast" [](https://expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) ![Red Roof Inn & Suites Chestertown](//images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "Room temperature was good. Room was also very spacious and clean. " [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](//images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "N/A" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](//images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Pleasant staff. Very accommodating." [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chestertown? > [Red Roof Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information): Offers full, a seasonal outdoor pool, and free self parking. [Comfort Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information): Provides 3 bars, a seasonal outdoor pool, and free self parking. [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information): Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. [Historic Inns of Annapolis](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information): Features complimentary wired internet access, an indoor pool, and free self parking. [Pendry Baltimore](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information): Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool, and free self parking. ### What is there to see and do in Chestertown? > Make a point to visit attractions like Chestertown Dog Park and Crumpton Auction. Discover sights such as Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Garfield Center for the Arts at the Prince Theater during your stay. ### When is the best time to book a hotel with a pool in Chestertown? > You may want to consider a place to stay that offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. 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