Title: Book the Best Hotels with POOL in Windham in 2026 | Expedia.ca [Windham Travel Guide](https://expedia.ca/Windham.dx175529)[Hotels in Windham](https://expedia.ca/Windham-Hotels.d175529.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.ca/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.ca/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Windham Car Rentals](https://expedia.ca/Car-Rentals-In-Windham.d175529.Car-Rental-Guide)[Windham Vacation Packages](https://expedia.ca/Windham.d175529.Destination-Travel-Guides) ![Amazing foliage upstate New York. Morning sunlight spills over the golden foliage. Windham NY is one of the most popular destination for scenic drives, bike trails, foliage and nature lovers.; Shutter](https://images.trvl-media.com/place/175529/3d9b5210-4eb0-422c-87cb-eedcfc9fa09e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175529/3d9b5210-4eb0-422c-87cb-eedcfc9fa09e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Windham Hotels with a Pool Tonight [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-13&endDate=2026-01-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windham hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/23d7c707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/89295c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/aab44153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vienna [](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) Windham 9.4/10 Exceptional (739 reviews) "Great service, nice and clean hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $199 CA $214 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/79463c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/4da17503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/d6f0773d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/6a98f43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Hotel Windham [](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) Windham 8.6/10 Excellent (92 reviews) "Very nice hotel. Exactly what we needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicolas CA $243 CA $332 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Japanese Futon](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/738c735e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/604935bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/06763b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) Windham 8.8/10 Excellent (344 reviews) "convenient nice and clean residence with kitchen and market nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jatin CA $262 CA $283 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Classic Double Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/2fb255db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/331aec89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/d8dfd254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/608feb4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Outpost by Windham Mountain Club [](https://www.expedia.ca/Windham-Hotels-The-Outpost-By-Windham-Mountain-Club.h118922119.Hotel-Information) Windham 8.6/10 Excellent (4 reviews) "Cozy and warm. I think it would be better to visit during the winter season" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TAEJUN CA $347 CA $375 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Windham-Hotels-The-Outpost-By-Windham-Mountain-Club.h118922119.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/17883b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/c3080178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/5314e9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/30995893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven [](https://www.expedia.ca/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) Windham 10/10 Exceptional (3 reviews) "Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael L. CA $1,006 CA $1,924 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/123000000/122310000/122309300/122309290/w1430h949x0y0-ddefed88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122310000/122309300/122309290/w1430h949x0y0-4269ec88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122310000/122309300/122309290/8dac696b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122310000/122309300/122309290/f9ba3577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome [](https://www.expedia.ca/Windham-Hotels-Windham-Mountain-Slope-Side-Escape-W-Private-Hot-Tub-Pets-Welcome.h122309290.Hotel-Information) Windham 8.0/10 Very good (1 review) "We loved ,.. place was very clean and organized " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristina L. CA $301 CA $765 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Windham-Hotels-Windham-Mountain-Slope-Side-Escape-W-Private-Hot-Tub-Pets-Welcome.h122309290.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/b1665fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/ba972182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/w1170h876x0y33-83e5059b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/ea784583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Windham Mountain Village [](https://www.expedia.ca/Windham-Hotels-Condo-In-Windham-Mountain-Village.h72533237.Hotel-Information) Windham 10/10 Exceptional (14 reviews) "Place was amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erik B. CA $923 CA $1,419 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Windham-Hotels-Condo-In-Windham-Mountain-Village.h72533237.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/213defa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/da2fe2a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/8751513e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/78103f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Motel [](https://www.expedia.ca/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) Grand Gorge 9.4/10 Exceptional (412 reviews) "Awesome place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $124 CA $136 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/a20af6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/0d893f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/10cb851a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/eb4d41ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moore's Motel [](https://www.expedia.ca/Prattsville-Hotels-Moores-Motel.h16545641.Hotel-Information) Prattsville 8.6/10 Excellent (160 reviews) "No frills, great value, friendly owners, clean rooms, hot showers with great pressure, heat worked well. Will return. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $167 CA $180 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Prattsville-Hotels-Moores-Motel.h16545641.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/45e16787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/9de41546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/69ba57d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow | Living area](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/4d574ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Graham & Co. [](https://www.expedia.ca/Phoenicia-Hotels-The-Graham-Co.h17412349.Hotel-Information) Phoenicia 9.6/10 Exceptional (22 reviews) "Amazing rustic getaway. They go above and beyond to ensure you are taken care of. Absolutely great experience, highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mutasar CA $215 CA $241 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Phoenicia-Hotels-The-Graham-Co.h17412349.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=2026-01-27&endDate=2026-01-28®ionId=175529&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Hotel Reviews ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "We stay here often and always have a great experience. Clean room,super comfortable bed and friendly staff (especially the sweet blonde lady that works Sunday night and Monday morning-it skipped my mind to ask what her name was but she is very nice every time). " [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Howard Johnson by Wyndham Saugerties](https://images.trvl-media.com/lodging/1000000/30000/20500/20423/2cdc8bdd_y.jpg) ### Howard Johnson by Wyndham Saugerties 10/10 Excellent "Did pre-checkin, and when I arrived it was such a quick process. " [](https://expedia.ca/Kingston-Hotels-Howard-Johnson-By-Wyndham-Saugerties.h20423.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Windham? ### What is there to see and do in Windham? ### When is the best time to book a hotel with a pool in Windham? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in East Windham ](https://www.expedia.ca/4Star-East-Windham-Hotels.s40-0-d183666.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Hensonville ](https://www.expedia.ca/4Star-Hensonville-Hotels.s40-0-d6023521.Travel-Guide-Filter-Hotels) - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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