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Hotels with Swimming Pool in Windham, New York

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Check availability on Windham Hotels with Swimming Pool

Tonight
Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.
A cabin with a deck, large windows, and a mountain backdrop.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
P6,577
P8,185 total
includes taxes & fees
Oct 6 - Oct 7
Hotel Vienna
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

2. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
P16,748
P21,216 total
includes taxes & fees
Oct 29 - Oct 30
Wylder Hotel Windham
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 compact living space with a kitchen, dining area, and seating.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
P7,928
P8,563 total
includes taxes & fees
Nov 1 - Nov 2
The Winwood Condominiums
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
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.
A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

4. 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.
P11,154
P13,282 total
includes taxes & fees
Nov 2 - Nov 3
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with lounge chairs and potted plants.
A two-story motel with a central staircase, balconies, and a grassy front yard.
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.

5. 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.
P7,506
P8,107 total
includes taxes & fees
Oct 6 - Oct 7
Moore's Motel
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".

6. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
P5,573
P6,130 total
includes taxes & fees
Oct 6 - Oct 7
The Colonial Motel
A swimming pool with lounge chairs and umbrellas.
A cozy living room with a plaid sofa, a fireplace, and various decorative items on shelves above the fireplace.
A buffet table with various food items and a painting on the wall.
A sign for Crystal Brook Resort surrounded by red tulips.

7. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
P13,636
P14,727 total
includes taxes & fees
Oct 30 - Oct 31
Crystal Brook Resort & Mountain Brauhaus
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A stone building with a chimney, a pool, and a sign for Shandaken Inn.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
P8,895
P9,963 total
includes taxes & fees
Nov 1 - Nov 2
Shandaken Inn
An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.
A hotel room with a bed, a desk, a sofa, and two lamps.
A reception area with a wooden reception desk, a television mounted on the wall, a blue sofa, and a fireplace with plants.
A hotel room with a bed, desk, chair, TV, and kitchenette.

9. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Dive into refreshing aquatic relaxation at this Saugerties retreat featuring an indoor pool open daily from morning until evening.
P8,454
P9,468 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn Saugerties
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

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

10/10 Excellent
"Clean and well maintained hotel."
Uri 1-night trip
Posted 4 hours ago
Spark by Hilton West Coxsackie
Hotel Vienna

Hotel Vienna

8/10 Good
"Very clean and well kept place. The pool area is lovely as well. The breakfast was mostly sugar stuff though… with lots of pastries and sweetened yogurts, and only caffeinated coffee available. Be sure to prepare accordingly if you have dietary restrictions. We enjoyed our stay and the location."
Cindi 1-night trip
Posted 6 hours ago
Hotel Vienna
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"The room was clean and staff very pleasant and helpful. I would stay again."
Shirley 1-night trip
Posted 9 hours ago
Howard Johnson by Wyndham Saugerties

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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