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

Find Hotels with a Pool in Windham, NY

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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 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 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.
$145 nightly
$157 total
Oct 29 - Oct 30
Total with taxes and fees
Hotel Vienna
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 kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.
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 splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
$167 nightly
$180 total
Oct 19 - Oct 20
Total with taxes and fees
The Winwood Condominiums
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.
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.
$271 nightly
$293 total
Oct 29 - Oct 30
Total with taxes and fees
Wylder Hotel Windham
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 modern building with large windows, a covered outdoor area with seating, and a pool.
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
$447 nightly
$483 total
Nov 3 - Nov 4
Total with taxes and fees
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 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.

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.
$916 nightly
$989 total
Oct 15 - Oct 16
Total with taxes and fees
Condo in Windham Mountain Village
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A covered porch with outdoor seating, a staircase, and potted plants.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
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.
$77 nightly
$85 total
Oct 15 - Oct 16
Total with taxes and fees
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 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.

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.
$202 nightly
$220 total
Nov 12 - Nov 13
Total with taxes and fees
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 hotel room with two beds, a desk, a chair, and a TV on a stand.
A two-story building with a large front porch, a chimney, and a balcony.

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.
$120 nightly
$130 total
Oct 15 - Oct 16
Total with taxes and fees
Moore's Motel
A log cabin with a porch, a staircase, and a garage.
An outdoor wicker furniture set with red cushions on a wooden deck.
A bathroom with a white sink, a shower curtain, and a tiled wall.
A kitchen with dark green cabinets, a tiled backsplash, a stainless steel sink, and a decorative Buddha head.

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

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
$206 nightly
$222 total
Oct 18 - Oct 19
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.
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.

10. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
$158 nightly
$177 total
Oct 27 - Oct 28
Total with taxes and fees
Shandaken Inn
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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 3 days ago
Hotel Vienna

Frequently asked questions

How much does a hotel with outdoor pool in Windham cost?
Enjoy staying in a hotel in Windham with an outdoor pool. You can find a great deal from $85 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Windham with outdoor pool activities or events?
Windham, New York, is a charming mountain town known for its stunning natural landscapes and outdoor activities. Travellers seeking a refreshing retreat will be pleased to discover that several hotels in the area offer outdoor pool activities. The Wylder Windham stands out as a fantastic option, featuring a heated outdoor pool complemented by wood-fired barrel saunas, superb for unwinding after a day of hiking or skiing.For families, the Winwood Inn & Condominiums is another excellent choice, boasting an outdoor pool that is open during the summer season. This welcoming atmosphere, combined with spacious rooms, makes it an ideal spot for families looking to relax and enjoy quality time together.
Is it cheaper to book flights and a Windham hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Windham for you.

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