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Check availability on Windham Hotels with a Pool

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
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 cabin with a deck, large windows, and a mountain backdrop.
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.
￥15,681
￥19,664 total
includes taxes & fees
Oct 29 - Oct 30
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 modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.
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.
￥39,845
￥50,949 total
includes taxes & fees
Oct 11 - Oct 12
Wylder Hotel Windham
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 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.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
￥26,685
￥28,820 total
includes taxes & fees
Nov 1 - Nov 2
The Winwood Condominiums
An indoor swimming pool area with a hot tub, seating, and a caution sign.
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.
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
￥25,488
￥76,426 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 kitchen with wooden cabinets, a dining area with a wooden table and chairs, and a hanging light fixture.
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.

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.
￥105,004
￥162,688 total
includes taxes & fees
Oct 13 - Oct 14
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 cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.
A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

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.
￥28,230
￥33,618 total
includes taxes & fees
Nov 10 - Nov 11
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.
A modern breakfast area with a coffee machine, cereal, and bakery options.
A modern lobby with a reception desk, seating area, and a dining section.
A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

7. 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.
￥20,105
￥22,520 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
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 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 white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

8. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
￥12,240
￥13,463 total
includes taxes & fees
Oct 26 - Oct 27
The Colonial Motel
A swimming pool with lounge chairs and potted plants.
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.
A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.

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.
￥18,948
￥20,464 total
includes taxes & fees
Oct 16 - Oct 17
Moore's Motel
A log cabin with a porch, a staircase, and a garage.
A kitchen with dark green cabinets, a tiled backsplash, a stainless steel sink, and a decorative Buddha head.
A living room with a flat-screen TV on a wooden stand, a fireplace, a clock, and two framed artworks on the wall.
A bathroom with a white sink, a shower curtain, and a tiled wall.

10. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
￥20,580
￥35,221 total
includes taxes & fees
Oct 13 - Oct 14
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
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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

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 6 days 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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