A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Check availability on Windham Hotels with a Pool

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Windham hotels with a pool

A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.
A log cabin with a deck, outdoor seating, and a view of a forest.
A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.
A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
￥18,010
￥22,218 total
includes taxes & fees
Sep 2 - Sep 3
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A two-story building with a balcony, surrounded by well-maintained lawns and trees.
A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.
A compact living space with a kitchen, dining area, and seating.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
￥28,618
￥30,906 total
includes taxes & fees
Sep 2 - Sep 3
The Winwood Condominiums
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
￥40,888
￥52,148 total
includes taxes & fees
Sep 2 - Sep 3
Wylder Hotel Windham
An indoor swimming pool area with a hot tub, seating, and a caution sign.
A spacious living area with a sectional sofa, a wooden coffee table, and a kitchen in the background.
A spacious living area with a wooden staircase, a dining area, and a kitchen in the background.
A modern building with large windows, a covered outdoor area with seating, and a pool.

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
￥33,619
￥87,313 total
includes taxes & fees
Sep 14 - Sep 15
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.
A residential area with houses, a pond, and a large tree.
A tranquil lakeside view with a wooden bench, a tree, and a row of houses with steep roofs.
A modern two-story building with a blue door and large windows.

5. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
￥72,041
￥105,814 total
includes taxes & fees
Sep 2 - Sep 3
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.
A bedroom with a large bed, a desk, and two lamps.
A modern house with a large pond, a grassy area, and a clear sky.
A kitchen with wooden cabinets, a dining area with a wooden table and chairs, and a hanging light fixture.

6. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
  • Mountain village condo offers ski-in/ski-out access, heated pool, and hot tub for year-round adventures.
￥76,043
￥128,463 total
includes taxes & fees
Sep 7 - Sep 8
Condo in Windham Mountain Village
A swimming pool with lounge chairs and a covered seating area, surrounded by trees.
A cozy log cabin interior with a stone fireplace, wooden furniture, and large windows offering a mountain view.
A wooden cabin with a circular interior, a deck, and outdoor seating.
A wooden dining area with a fireplace, large windows, and a chandelier.

7. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
  • Luxury mountain chalet offers year-round aquatic adventure with outdoor pool, hot tub, and water park.
￥156,195
￥300,537 total
includes taxes & fees
Sep 13 - Sep 14
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
A large hotel with multiple floors, a parking lot, and a mountainous backdrop.
A cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.
A multi-story building with outdoor seating and a stone-paved patio.

8. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
￥29,999
￥35,723 total
includes taxes & fees
Sep 30 - Oct 1
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with lounge chairs and potted plants.
A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.
A hotel room with two beds, a desk, a chair, and a TV on a stand.
A two-story building with a large front porch, a chimney, and a balcony.

9. Moore's Motel

Moore's Motel
Prattsville
  • Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
￥19,175
￥20,709 total
includes taxes & fees
Sep 2 - Sep 3
Moore's Motel
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A covered porch with outdoor seating, a staircase, and potted plants.
A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

10. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
￥13,952
￥15,347 total
includes taxes & fees
Sep 10 - Sep 11
The Colonial Motel
View all properties

Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Windham Hotel Reviews

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Clean comfortable room and restaurant."
Richard 1-night trip
Posted 8 hours ago
Howard Johnson by Wyndham Saugerties
Hotel Vienna

Hotel Vienna

10/10 Excellent
"We really enjoyed the experience."
David 2-night trip
Posted 1 day ago
Hotel Vienna
The Graham & Co.

The Graham & Co.

10/10 Excellent
"Wonderful Stay"
Daniel 2-night trip
Posted 6 days ago
The Graham & Co.

Frequently asked questions

What are some accommodations with pools in Windham?
Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Features free self parking, a seasonal outdoor pool, and complimentary bicycles. Hotel Vienna: Hotel located near Windham Mountain Resort. Offers daily, an indoor pool, and free self parking. Eastwind Windham: Hotel located near Windham Mountain Resort. Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Jimmy OConnors Windham Mountain Inn: Hotel, 1-minute walk from Hunter Mountain. Features 2 hot tubs, an outdoor pool, and a sauna. The Haüs Windham: Offers a full-service spa, a seasonal outdoor pool, and complimentary bicycles.
What is there to see and do in Windham?
Surround yourself with nature at Elm Ridge Wild Forest and Ashland Park. During your stay, check out sights such as Windham Country Club, Windham Mountain Resort, and Catskill State 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.

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