Title: Book the Best Hotels with INDOOR 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 an Indoor Pool in Chestertown, MD from CA $109 - ![](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 an Indoor Pool Tonight [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-27&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-28&endDate=2025-12-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels with an indoor pool ![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) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.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 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) Chestertown 9.6/10 Exceptional (108) "Amazing and neat and very private " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander M. CA $135 CA $217 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two queen studio suite](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/4152f194.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) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Edgewood/Aberdeen-South [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) Edgewood 9.2/10 Wonderful (1004) "Room was great staff friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $114 CA $128 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![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) ![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) ### 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 (325) "Clean room, great staff, recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $148 CA $164 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/6af27243.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) ### 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 (651) "Room was great the staff is so friendly every visit !!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis CA $123 CA $137 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/3c250b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/88d1de79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/6380c7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/36fcefa1.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 (634) "Close to restaurants, friendly staff, nice room, food was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy CA $132 CA $147 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/48ed0abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/7074520f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/18db37ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/ae4c61bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Baltimore / Aberdeen, MD [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) Aberdeen 8.8/10 Excellent (339) "Clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $98 CA $109 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/7daf57ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/e5cd056f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/bcb2d6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/86edcd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Edgewood Aberdeen [](https://www.expedia.ca/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) Aberdeen 9.0/10 Wonderful (96) "Spotless, very good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Efrain CA $149 CA $167 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/47756559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/0ab02da4.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/16000000/16000000/15990300/15990289/6d549ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.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 (606) "very pet friendly!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) larry CA $134 CA $150 total includes taxes & fees Jan 17 - Jan 18, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/f6ab6350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/6f1191b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/7061f83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/6b59ba72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Aberdeen at Ripken Stadium [](https://www.expedia.ca/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.Hotel-Information) Aberdeen 8.6/10 Excellent (219) "We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $115 CA $129 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/bdf87bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/e60ed5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (680) "The staff are the absolute best. Our room was perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $159 CA $176 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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=2026-01-10&endDate=2026-01-11®ionId=7215&adults=2&property_amenities_group_explore=indoor_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 "All-round amazing" [](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 "The omelet was tasty." [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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 "The chef was amazing" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Very nice" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.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 "Always a pleasure dealing with Best Western!!" [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "room was clean but the shower curtain was in tatters. multiple rings torn off" [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ## Frequently asked questions ### What does Chestertown have to offer on top of hotels with indoor pools? ### What is there to do in Chestertown? ### Why should I choose a hotel with an indoor pool for my stay 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) - 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