Title: The Best Hotels with a Pool in Chestertown from $92 in 2026 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx89045)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d89045.Destination-Travel-Guides) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check availability on Chestertown Hotels with a Pool Tonight [Mar 2 - Mar 3](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-02&endDate=2026-03-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 3 - Mar 4](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-03&endDate=2026-03-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels with a pool ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19960000/19955100/19955012/fc6e0b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/20000000/19960000/19955100/19955012/3b9531ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/20000000/19960000/19955100/19955012/aff0a089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19960000/19955100/19955012/82b0b507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lily Pad North at Loon Lake near Gore Mountain [](https://www.expedia.com/Chestertown-Hotels-Lily-Pad-North-At-Loon-Lake-Near-Gore-Mountain.h19955012.Hotel-Information) Chestertown 9.6/10 Exceptional (30 reviews) $247 nightly $274 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Chestertown-Hotels-Lily-Pad-North-At-Loon-Lake-Near-Gore-Mountain.h19955012.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/a91c67c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/2f07bb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/790ff6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/01f531cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Queensbury Hotel [](https://www.expedia.com/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) Glens Falls 9.4/10 Exceptional (1,531 reviews) - Vintage charm meets aquatic bliss in this Victorian hotel with an indoor pool, hot tub, and health club to revitalize. $109 nightly $121 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/59b5e6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/8b8d1fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/7c36798c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fort William Henry Hotel and Conference Center [](https://www.expedia.com/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) Lake George 8.6/10 Excellent (1,003 reviews) - Refreshing lake views paired with year-round swimming options make this resort perfect for water lovers seeking mountain scenery. $115 nightly $127 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/87c2f85e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Lake View (Balcony) | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/db6cb3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Lake View (Balcony) | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/6dc91933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Lake George [](https://www.expedia.com/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) Lake George 9.2/10 Wonderful (1,001 reviews) - Dive into aquatic bliss at this hotel's indoor pool sanctuary, open year-round regardless of weather. $112 nightly $124 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/ab1128e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/8b1d260e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/66a73c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/0dae3ead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY [](https://www.expedia.com/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) Queensbury 9.0/10 Wonderful (1,363 reviews) - Splashy mountain escapes await at this inviting retreat with indoor and outdoor pools. $88 nightly $98 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/85a37759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/8e42b71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/5f6f7e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/a4ce53b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Lake George [](https://www.expedia.com/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) Lake George 8.8/10 Excellent (1,682 reviews) - Splash into family fun at this Lake George hotel with an indoor pool, waterslide, and hot tub. $101 nightly $112 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/e16443c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/2a07a8bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/80e9c724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/5b03322e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Lake George - Adirondack Area by IHG [](https://www.expedia.com/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) Lake George 9.2/10 Wonderful (1,005 reviews) - Pool paradise awaits with year-round swimming options at this mountain resort hotel. $97 nightly $108 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/3719d452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/a8a5ec23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/e8c3fc23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Six Flags Great Escape Lodge & Indoor Waterpark [](https://www.expedia.com/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) Queensbury 8.0/10 Very Good (1,535 reviews) - Splash into adventure at a family-friendly water resort with thrilling slides and a lazy river. $132 nightly $147 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Indoor pool, outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/e1f93c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/e1ad3c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/5f75ab9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/b3fb7cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western of Lake George [](https://www.expedia.com/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) Lake George 7.8/10 Good (1,002 reviews) - Splash into poolside paradise at Lake George with sun loungers and mountain views. $83 nightly $92 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/3df870ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/0f42a582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, One King Bed, Non-Smoking | Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/9670914a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Lake George [](https://www.expedia.com/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) Lake George 8.8/10 Excellent (1,003 reviews) - Plunge into relaxation at this family-friendly retreat with an inviting indoor pool, hot tub, and well-equipped fitness center. $98 nightly $108 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.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=2026-03-17&endDate=2026-03-18®ionId=89045&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Chestertown Breakfast included Hot tub 4 stars 5 stars 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_89045) ## Top Chestertown Hotel Reviews ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/8795775f_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Excellent hotel with great breakfast" [](https://expedia.com/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "The rooms are very clean and the staff there is always awesome and very pleasant." [](https://expedia.com/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Courtyard by Marriott Lake George](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "Clean. Friendly. All good. " [](https://expedia.com/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "The staff was great." [](https://expedia.com/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Hampton Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456_y.jpg) ### Hampton Inn & Suites Lake George 10/10 Excellent "Everything was great" [](https://expedia.com/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Best Western of Lake George](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/e1f93c73_y.jpg) ### Best Western of Lake George 10/10 Excellent "Friendly staff!" [](https://expedia.com/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/8b8d1fb3_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Room was nice and cozy. Staff was friendly and helpful." [](https://expedia.com/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "Staff was amazing, breakfast great, and the room was so clean. We only had one problem and that was with another guest who was rude. So i would stay there again. " [](https://expedia.com/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Comfort Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg) ### Comfort Inn & Suites Lake George 10/10 Excellent "Great location, clean, affordable, great front desk service and awesome breakfast " [](https://expedia.com/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information) ## Frequently asked questions ### What are some hotels 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 Rentals - [Hotels near Loon Lake Beach ](https://www.expedia.com/Loon-Lake-Beach-Hotels.0-l553248621554184980-0.Travel-Guide-Filter-Hotels) - [Family Hotels in Brant Lake ](https://www.expedia.com/Brant-Lake-Hotels-Family-Hotel.0-0-d6347839-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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