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Check availability on Windham Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.
A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.
A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
CA $149
CA $185 total
includes taxes & fees
Nov 10 - Nov 11
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A compact living space with a kitchen, dining area, and seating.
A two-story building with a balcony, surrounded by well-maintained lawns and trees.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
CA $240
CA $260 total
includes taxes & fees
Nov 1 - Nov 2
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 modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.
A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
CA $272
CA $365 total
includes taxes & fees
Oct 29 - Oct 30
Wylder Hotel Windham
An indoor swimming pool area with a hot tub, seating, and a caution sign.
A modern building with large windows, a covered outdoor area with seating, and a pool.
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.
A spacious living area with a sectional sofa, a wooden coffee table, and a kitchen in the background.

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
CA $230
CA $686 total
includes taxes & fees
Nov 3 - Nov 4
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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 room with a sloped ceiling, a flat-screen TV mounted on the wall, a bean bag chair, and a ceiling light fixture.
A modern house with a large pond, a grassy area, and a clear sky.

5. 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.
CA $946
CA $1,454 total
includes taxes & fees
Oct 15 - Oct 16
Condo in Windham Mountain Village
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
A cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.
A large hotel with multiple floors, a parking lot, and a mountainous backdrop.
A multi-story building with outdoor seating and a stone-paved patio.

6. 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.
CA $255
CA $303 total
includes taxes & fees
Nov 12 - Nov 13
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
A covered porch with outdoor seating, a staircase, and potted plants.
A cozy room with a white sofa, a wooden table with a lamp, and a chair with a patterned cushion. There's a reception desk with a computer and a sign that says "Welcome".

7. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
CA $109
CA $120 total
includes taxes & fees
Oct 18 - Oct 19
The Colonial Motel
A swimming pool with lounge chairs and potted plants.
A two-story building with a large front porch, a chimney, and a balcony.
A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.
A two-story motel with a central staircase, balconies, and a grassy front yard.

8. 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.
CA $171
CA $184 total
includes taxes & fees
Oct 15 - Oct 16
Moore's Motel
A swimming pool with lounge chairs and umbrellas.
A wooden lodge with a welcoming sign, a bear statue, and two flags.
A sign for Crystal Brook Resort surrounded by red tulips.
A cozy living room with a plaid sofa, a fireplace, and various decorative items on shelves above the fireplace.

9. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
CA $310
CA $335 total
includes taxes & fees
Oct 30 - Oct 31
Crystal Brook Resort & Mountain Brauhaus
A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.
A modern lobby with a reception desk, seating area, and a dining section.
A modern breakfast area with a coffee machine, cereal, and bakery options.

10. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Saugerties
  • Dive into refreshing escapes at this indoor pool sanctuary with post-adventure relaxation vibes.
CA $181
CA $203 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
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Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Windham Hotel Reviews

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. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Jimmy OConnors Windham Mountain Inn: Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. The Haüs Windham: Hotel, 1-minute walk from Hunter Mountain. Provides 2 hot tubs, an outdoor pool, and a sauna.
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 Windham Vineyards and Winery. 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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