Title: The Best Hotels with a Pool in Windham from $98 in 2026 | Expedia.com [Windham Travel Guide](https://expedia.com/Windham.dx175529)[Hotels in Windham](https://expedia.com/Windham-Hotels.d175529.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.com/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.com/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.com/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Car Rentals in Windham](https://expedia.com/Car-Rentals-In-Windham.d175529.Car-Rental-Guide)[Windham Vacation Packages](https://expedia.com/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) ## Check availability on Windham Hotels with a Pool Tonight [Mar 4 - Mar 5](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-03-04&endDate=2026-03-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 5 - Mar 6](https://www.expedia.com/Hotel-Search?regionId=175529&startDate=2026-03-05&endDate=2026-03-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=175529&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=175529&startDate=2026-03-13&endDate=2026-03-15&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/1000000/900000/893300/893228/89295c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/f91cd0d7.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) ### Hotel Vienna [](https://www.expedia.com/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) Windham 9.4/10 Exceptional (775 reviews) - Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers. $149 nightly $161 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/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) ![The Windham Mountain View King with Balcony | In-room safe, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/4da17503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Hotel Windham [](https://www.expedia.com/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) Windham 8.6/10 Excellent (93 reviews) - Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation. $214 nightly $231 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/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) ![Exterior](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/06763b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Japanese Futon | Blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/738c735e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Winwood Condominiums by Windham Mountain Club [](https://www.expedia.com/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) Windham 8.6/10 Excellent (350 reviews) - Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options. $169 nightly $183 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Classic Double Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets](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 | Combined shower/tub, hair dryer, towels, soap](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.com/Windham-Hotels-The-Outpost-By-Windham-Mountain-Club.h118922119.Hotel-Information) Windham 8.4/10 Very Good (5 reviews) - Alpine retreat near Windham Mountain offers free ski shuttle, seasonal outdoor pool, and slope-side relaxation. $250 nightly $270 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Windham-Hotels-The-Outpost-By-Windham-Mountain-Club.h118922119.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) ![Dining](https://images.trvl-media.com/lodging/73000000/72540000/72533300/72533237/w1170h876x0y33-83e5059b.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) ![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.com/Windham-Hotels-Condo-In-Windham-Mountain-Village.h72533237.Hotel-Information) Windham 10/10 Exceptional (15 reviews) - Mountain village condo offers ski-in/ski-out access, heated pool, and hot tub for year-round adventures. $626 nightly $676 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Windham-Hotels-Condo-In-Windham-Mountain-Village.h72533237.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) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122310000/122309300/122309290/f9ba3577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122310000/122309300/122309290/44062bf6.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) ### Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome [](https://www.expedia.com/Windham-Hotels-Windham-Mountain-Slope-Side-Escape-W-Private-Hot-Tub-Pets-Welcome.h122309290.Hotel-Information) Windham 9.6/10 Exceptional (4 reviews) $529 nightly $571 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Windham-Hotels-Windham-Mountain-Slope-Side-Escape-W-Private-Hot-Tub-Pets-Welcome.h122309290.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/112000000/111590000/111585700/111585672/30995893.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) ![Dining](https://images.trvl-media.com/lodging/112000000/111590000/111585700/111585672/d4ed943f.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.com/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.Hotel-Information) Windham 10/10 Exceptional (7 reviews) - Luxury mountain chalet offers year-round aquatic adventure with outdoor pool, hot tub, and water park. $1,381 nightly $1,491 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Windham-Hotels-Luxury-3300-Sqft-Chalet.h111585672.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/78103f2a.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) ### The Colonial Motel [](https://www.expedia.com/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) Grand Gorge 9.6/10 Exceptional (426 reviews) - Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat. $89 nightly $98 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/d6e9603b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/fbbd36bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/c39e9582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, steam room, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/f1e8860d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Emerson Resort & Spa [](https://www.expedia.com/Kingston-Hotels-Emerson-Resort-Spa.h38028935.Hotel-Information) Mount Tremper 9.4/10 Exceptional (53 reviews) - Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains. $180 nightly $202 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Emerson-Resort-Spa.h38028935.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=2026-03-18&endDate=2026-03-19®ionId=175529&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Windham 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_175529) ## Top Windham Hotel Reviews ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/f91cd0d7_y.jpg) ### Hotel Vienna 10/10 Excellent "A perfect location to hit the slopes! We loved the breakfast and the sauna the most. The room was very nicely decorated and comfy too. Would definitely stay here again for future outdoor adventures in the Catskills. " [](https://expedia.com/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ## Frequently asked questions ### How much does a hotel with outdoor pool in Windham cost? ### Are there hotels in Windham with outdoor pool activities or events? > For families, the Winwood Inn & Condominiums is another excellent choice, boasting an outdoor pool that is open during the summer season. This welcoming atmosphere, combined with spacious rooms, makes it an ideal spot for families looking to relax and enjoy quality time together. ### Is it cheaper to book flights and a Windham hotel with a pool as a package? ### How can I save on a Windham hotel with a pool with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Windham Country Club ](https://www.expedia.com/Windham-Country-Club-Hotels.0-l553248621552322141-0.Travel-Guide-Filter-Hotels) - [Hotels near Windham Mountain Resort ](https://www.expedia.com/Windham-Mountain-Resort-Hotels.0-l6087209-0.Travel-Guide-Filter-Hotels) - [Hensonville Hotels ](https://www.expedia.com/Hensonville-Hotels.d6023521.Travel-Guide-Hotels) - [Apartments in Hensonville ](https://www.expedia.com/Hensonville-Apartments.d6023521-aaApartments.Travel-Guide-Accommodation) - [B&B in Hensonville ](https://www.expedia.com/Hensonville-Bed-And-Breakfast.d6023521-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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