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

Windham Hotel Guide - Hotels with Pool in Windham, New York

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Check availability on Windham Hotels with Pool

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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.
€111
includes taxes & fees
29 Oct - 30 Oct
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.
A compact living space with a kitchen, dining area, and seating.
A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
€163
includes taxes & fees
1 Nov - 2 Nov
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 restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
€303
includes taxes & fees
13 Oct - 14 Oct
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 wooden staircase, a kitchen in the background, and a large window providing a view of the outdoors.

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
€428
includes taxes & fees
9 Nov - 10 Nov
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 modern house with a large pond, a grassy area, and a clear sky.
A room with a sloped ceiling, a flat-screen TV mounted on the wall, a bean bag chair, and a ceiling light fixture.
A kitchen with wooden cabinets, a dining area with a wooden table and chairs, and a hanging light fixture.

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.
€961
includes taxes & fees
12 Nov - 13 Nov
Condo in Windham Mountain Village
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.
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".
A covered porch with outdoor seating, a staircase, and potted plants.

6. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
€88
includes taxes & fees
14 Oct - 15 Oct
The Colonial Motel
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.
A multi-story building with outdoor seating and a stone-paved patio.
A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

7. 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.
€190
includes taxes & fees
10 Nov - 11 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
€142
includes taxes & fees
27 Oct - 28 Oct
Shandaken Inn
A log cabin with a porch, a staircase, and a garage.
A bathroom with a white sink, a shower curtain, and a tiled wall.
An outdoor wicker furniture set with red cushions on a wooden deck.
A living room with a flat-screen TV on a wooden stand, a fireplace, a clock, and two framed artworks on the wall.

9. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
€203
includes taxes & fees
13 Oct - 14 Oct
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
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 two-story motel with a central staircase, balconies, and a grassy front yard.
A hotel room with two beds, a desk, a chair, and a TV on a stand.

10. 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.
€116
includes taxes & fees
13 Oct - 14 Oct
Moore's Motel
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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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Hotel was clean, had pretty Catskills Mountains views, and fire pits, pool and sauna. Staff was helpful."
Glenn 1-night trip
Posted 17 hours ago
Hotel Vienna

Frequently asked questions

What are some accommodation options 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, visit sights such as Windham Country Club, Windham Mountain Resort and Windham Vineyards and Winery. The mountain views, skiing and coffee shops 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 the local weather in Windham into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.