Find Hotels with a Pool in Windham, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Hotels with a Pool

Top Windham Hotels with a Pool

Pool
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham
  • Hot tub
$438 nightly
The price is $473
Nov 17 - Nov 18
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Indoor pool
Hotel Vienna

Hotel Vienna

2.5 star property
Windham
  • Indoor pool
9.4 out of 10, Exceptional, (698)
Crystal-clear waters beckon at the indoor aquatic sanctuary, perfect for unwinding after mountain adventures. Complimentary bicycles await outside while spotless rooms offer balconies overlooking breathtaking woodland scenery and nearby ski slopes.
$111 nightly
The price is $120
Nov 19 - Nov 20
Total with taxes and fees
Hotel Vienna
Outdoor pool
Wylder Hotel Windham

Wylder Hotel Windham

3.5 star property
Windham
  • Outdoor pool
8.8 out of 10, Excellent, (79)
Seasonal outdoor pool creates a refreshing summer sanctuary after exploring nearby mountain trails. Beyond swimming, guests enjoy complimentary bicycles, an on-site restaurant with happy hour, and cozy rooms equipped with bathrobes and modern comforts.
$225 nightly
The price is $243
Nov 14 - Nov 15
Total with taxes and fees
Wylder Hotel Windham
Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3.0 star property
Windham
  • Pool
  • Parking included
  • Free WiFi
  • Game room
  • Laundry
  • Housekeeping
8.8 out of 10, Excellent, (343)
Mountainside relaxation awaits at the seasonal outdoor pool, perfect for summer splashes between skiing adventures. With ski shuttle service, passes, and nearby hiking trails, this hotel balances aquatic refreshment with alpine exploration.
$169 nightly
The price is $183
Nov 16 - Nov 17
Total with taxes and fees
Winwood Condominiums by Windham Mountain Club
Condo, Mountain View | Iron/ironing board, free WiFi
Mountainside by Windham Mountain Club

Mountainside by Windham Mountain Club

3.0 star property
Windham
  • Outdoor pool
  • 2 hot tubs
Aquatic bliss awaits at the refreshing outdoor pool, available from 8:00 AM to 8:00 PM, complemented by 2 soothing hot tubs. Après-ski indulgence extends to the full-service spa offering Swedish massages near Windham Mountain Resort.
$1,320 nightly
The price is $1,426
Nov 14 - Nov 15
Total with taxes and fees
Mountainside by Windham Mountain Club
Lobby sitting area
The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club

2.5 star property
Windham
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
8.0 out of 10, Very Good, (3)
Splash into summer adventures at the seasonal outdoor pool, open May through September for sun-soaked relaxation after mountain excursions. Winter transforms this alpine retreat into a skier's paradise with complimentary shuttle service to nearby slopes.
$199 nightly
The price is $215
Nov 26 - Nov 27
Total with taxes and fees
The Outpost by Windham Mountain Club
Outdoor pool, a heated pool
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Windham
  • Outdoor pool
  • Hot tub
10.0 out of 10, Exceptional, (3)
Mountain adventures continue poolside at this recreational chalet. Swimmers enjoy an outdoor pool and water park, while the hot tub and sauna provide après-ski relaxation. Winter sports, hiking trails, and a game room ensure entertainment in every season.
$1,339 nightly
The price is $1,447
Nov 19 - Nov 20
Total with taxes and fees
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Exterior
Condo in Windham Mountain Village

Condo in Windham Mountain Village

Windham
  • Hot tub
10.0 out of 10, Exceptional, (14)
Heated pool waters welcome tired muscles after days spent exploring nearby Windham Mountain trails. Skiers appreciate the convenient ski-on/off access, while summer visitors enjoy proximity to beautiful golf courses just 5 minutes away.
$705 nightly
The price is $761
Nov 16 - Nov 17
Total with taxes and fees
Condo in Windham Mountain Village
Seasonal outdoor pool, pool umbrellas, sun loungers
The Colonial Motel

The Colonial Motel

2.5 star property
Grand Gorge
  • Pool loungers
9.4 out of 10, Exceptional, (402)
Surrounded by outdoor adventures from Mine Kill State Park to ski resorts, this motel offers a pristine seasonal pool complete with sun loungers and umbrellas. Clean, individually decorated rooms provide a cozy mountain retreat.
$99 nightly
The price is $109
Nov 17 - Nov 18
Total with taxes and fees
The Colonial Motel
Outdoor pool
Moore's Motel

Moore's Motel

2.5 star property
Prattsville
  • Outdoor pool
8.6 out of 10, Excellent, (158)
Crystal-clear waters beckon at the outdoor pool, where guests relish tranquil swims amid landscaped gardens. Barbecue grills nearby create opportunities for alfresco dining, complementing this exceptionally clean, comfortable retreat.
$120 nightly
The price is $130
Nov 16 - Nov 17
Total with taxes and fees
Moore's Motel
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

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Room was nice and clean. The staff was beyond friendly and made me feel comfortable and welcomed. Would definitely stay here again!"
Jessica 2-night trip
Posted 4 days ago
Hotel Vienna

Frequently asked questions

What are some accommodations with pools in Windham?
Hotel Vienna: Hotel located near Windham Mountain Resort. Features daily, an indoor pool, and free self parking. Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool, and complimentary bicycles. Eastwind Windham: 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: Hotel, 1-minute walk from Windham Mountain Resort. Features 2 restaurants, an outdoor pool, and a full-service spa. Albergo Allegria Hotel & Breakfast Restaurant: Hotel, 13-minute walk from Hunter Mountain. Features a sauna, an outdoor pool, and complimentary wireless internet access.
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