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Find Hotels with a Pool in Windham, NY

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Check availability on Windham Hotels with a Pool

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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 cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.
A cabin with a deck, large windows, and a mountain backdrop.
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.
₩136,750
₩171,478 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.
A two-story building with a balcony, surrounded by well-maintained lawns and trees.
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.
₩205,517
₩221,958 total
includes taxes & fees
Sep 20 - Sep 21
The Winwood Condominiums
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
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.
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.
₩351,196
₩447,445 total
includes taxes & fees
Sep 24 - Sep 25
Wylder Hotel Windham
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 hotel room with two beds, a desk, a chair, and a TV on a stand.

4. 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.
₩163,567
₩176,652 total
includes taxes & fees
Sep 18 - Sep 19
Moore's 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 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.

5. 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.
₩269,382
₩320,797 total
includes taxes & fees
Sep 22 - Sep 23
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 white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

6. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
₩121,449
₩133,580 total
includes taxes & fees
Sep 21 - Sep 22
The Colonial 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
"We had an amazing time at the Hotel Vienna. Jacob was the most amazing host and the breakfast was delicious and all of the amenities were fabulous. We could not have been happier. In the morning at 7:30 the entire hotel start smelling like fresh baked croissants. I am not a morning person, but this got me up every morning to go downstairs and enjoy their amazing breakfast. I can’t say enough about this hotel and how fabulous the staff is."
Jourdan 3-night trip
Posted 8 hours ago
Hotel Vienna
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"We stayed here once before. Staff were nice. Room was okay. Kinda old. But okay for a short stay. Internet was in and out. Bathroom water never got real hot for showers. Toilet was very low... my knees were in my mouth. The toilet bowl seat was close to broken. We MAY come back if necessary. Hopefully, some of our current concerns will be remedied. Thanks"
Richard 2-night trip
Posted 4 days ago
Howard Johnson by Wyndham Saugerties

Frequently asked questions

What are some accommodations with pools in Windham?
Hotel Vienna: Features daily, an indoor pool, and free self parking. Wylder Hotel Windham: Offers free self parking, a seasonal outdoor pool, and complimentary bicycles. Eastwind Windham: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Haüs Windham: Provides a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Jimmy OConnors Windham Mountain Inn: Features a sauna, an indoor pool, and free self parking.
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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