Title: Book the Best Hotels with POOL in Windham in 2025 | 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) ![](https://mediaim.expedia.com/destination/1/ebf6e8226484742f9fc98bf4b8dfb3d7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Windham, NY from CA $137 ![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 Windham Hotels with a Pool Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175529&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windham Hotels with a Pool ![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) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/d8569266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/929bed8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/119000000/118930000/118922200/118922119/084c3a26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Outpost by Windham Mountain Club Windham 8.0/10 Very good (3) "Cozy and warm. I think it would be better to visit during the winter season" CA $278 CA $300 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Windham-Hotels-The-Outpost-By-Windham-Mountain-Club.h118922119.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/c06d6be7.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/w750h561x0y0-3802df97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vienna Windham 9.4/10 Exceptional (657) "Great, clean hotel" [](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.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) ![1 bedroom, blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/ce5990b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Japanese Futon](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/97246a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/1ad206d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club Windham 8.8/10 Excellent (339) "No restaurant in property.only place for resting,sleeping." CA $250 CA $270 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Condo, Mountain View](https://images.trvl-media.com/lodging/119000000/118930000/118921800/118921772/ead25629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, Mountain View](https://images.trvl-media.com/lodging/119000000/118930000/118921800/118921772/75c899e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hot stone massages, deep-tissue massages, Swedish massages](https://images.trvl-media.com/lodging/119000000/118930000/118921800/118921772/ade64e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, Mountain View](https://images.trvl-media.com/lodging/119000000/118930000/118921800/118921772/483e1589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountainside by Windham Mountain Club Windham CA $1,842 CA $1,989 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Windham-Hotels-Mountainside-By-Windham-Mountain-Club.h118921772.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/103000000/102240000/102239500/102239431/6a98f43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Windham Mountain View King with Balcony](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/f3c6be8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Hotel Windham Windham 8.6/10 Excellent (71) "Absolutely friendly welcome in the Hotel, very good food, cozy and clean rooms, in a very nice area in the nature. Will get back to this place" CA $223 CA $311 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/63137643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/97b0013c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/b55d805a.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/f60b3dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven Windham 10/10 Exceptional (2) "Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful." CA $1,046 CA $2,117 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/w1024h632x0y25-73b2083f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/2f62e9d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/b16032cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/9c1b0b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Windham Mountain Village Windham 10/10 Exceptional (14) "Condo was clean and comfortable and very convenient to indoor pool and skiing. Thank you for a great vacation!" CA $534 CA $953 total includes taxes & fees Oct 28 - Oct 29 [](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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/8751513e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/18664b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/daa928ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Motel Grand Gorge 9.4/10 Exceptional (394) "Friendly quiet place. " CA $124 CA $137 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9550000/9542200/9542174/097af4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/10000000/9550000/9542200/9542174/7d70e6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9550000/9542200/9542174/w398h296x0y4-d35e4d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/10000000/9550000/9542200/9542174/w397h300x0y0-67d0b64f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Motel Catskill 8.2/10 Very good (198) "Very cute and cozy little motel. They put a lot of effort into cleaning and decorating each room. " CA $139 CA $151 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Kingston-Hotels-Four-Seasons-Motel.h9542174.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) ![Porch](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/3733bc8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/effd9ea0.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) ### Moore's Motel Prattsville 8.6/10 Excellent (152) "Stay here every time we are in the area. And its always a great stay and a good time down the street at the prattsville tavern. Moores is excellent" CA $167 CA $181 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Prattsville-Hotels-Moores-Motel.h16545641.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=2025-10-22&endDate=2025-10-23®ionId=175529&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Hotel Reviews ![Hotel Vienna](//images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Great, clean hotel" [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](//images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg) ### Holiday Inn Express Hotel & Suites West Coxsackie by IHG 10/10 Excellent "Room was clean, breakfast was great" [](https://expedia.ca/Albany-Hotels-Holiday-Inn-Express-Hotel-Suites-West-Coxsackie.h2591583.Hotel-Information) ![Howard Johnson by Wyndham Saugerties](//images.trvl-media.com/lodging/1000000/30000/20500/20423/2cdc8bdd_y.jpg) ### Howard Johnson by Wyndham Saugerties 10/10 Excellent "The pool was perfect!" [](https://expedia.ca/Kingston-Hotels-Howard-Johnson-By-Wyndham-Saugerties.h20423.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Windham? > [Hotel Vienna](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information): Hotel located near Windham Mountain Resort. Features daily, an indoor pool, and free self parking. [Eastwind Windham](https://www.expedia.ca/Windham-Hotels-Eastwind-Windham.h91907167.Hotel-Information): Hotel located near Windham Mountain Resort. Provides free self parking, a seasonal outdoor pool, and complimentary bicycles. [Wylder Hotel Windham](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information): Hotel located near Windham Mountain Resort. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Winwood Condominiums by Windham Mountain Club](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information): Hotel, 13-minute walk from Hunter Mountain. Features a sauna, an outdoor pool, and complimentary wireless internet access. [Albergo Allegria Hotel & Breakfast Restaurant](https://www.expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information): Features a sauna, an indoor pool, and free self parking. ### What is there to see and do in Windham? > Explore places like Hunter Mountain while you're in the area. Take in the natural beauty with a stop at Ashland Park. The mountain views, skiing, and coffeehouses are just some of the things to enjoy while you're in the area. ### When is the best time to book a hotel with a pool in Windham? > Taking into account the local weather in Windham is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall. ## 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) - [Hotels with Bar in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Bar.0-0-d603260-tHotelswithBar.Travel-Guide-Filter-Hotels) - 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