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 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 log cabin with a deck, outdoor seating, and a view of a forest.
A cabin with a deck, large windows, and a mountain backdrop.
A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
$151 nightly
$163 total
Oct 6 - Oct 7
Total with taxes and fees
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 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.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
$144 nightly
$155 total
Nov 1 - Nov 2
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.
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 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.
$361 nightly
$390 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 modern building with large windows, a covered outdoor area with seating, and a pool.
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 dining table, a sofa, a fireplace, and 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
$491 nightly
$530 total
Oct 27 - Oct 28
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.
A modern two-story building with a blue door and large windows.
A cozy living room with a sofa, a coffee table, and a lamp. There is a staircase leading to an upper level.
A residential area with houses, a pond, and a large tree.

5. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
$608 nightly
$657 total
Oct 5 - Oct 6
Total with taxes and fees
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
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 room with a sloped ceiling, a flat-screen TV mounted on the wall, a bean bag chair, and a ceiling light fixture.

6. 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.
$939 nightly
$1,014 total
Oct 5 - Oct 6
Total with taxes and fees
Condo in Windham Mountain Village
A swimming pool with lounge chairs and a covered seating area, surrounded by trees.
A cozy log cabin interior with a stone fireplace, wooden furniture, and large windows offering a mountain view.
Spacious living room with southern exposure and direct ski view
A wooden cabin with a circular interior, a deck, and outdoor seating.

7. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
  • Luxury mountain chalet offers year-round aquatic adventure with outdoor pool, hot tub, and water park.
$1,523 nightly
$1,644 total
Oct 5 - Oct 6
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
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 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.

8. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
$81 nightly
$89 total
Oct 5 - Oct 6
Total with taxes and fees
The Colonial Motel
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
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.
A multi-story building with outdoor seating and a stone-paved patio.

9. 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.
$197 nightly
$212 total
Nov 4 - Nov 5
Total with taxes and fees
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 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.
A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.

10. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
$158 nightly
$177 total
Nov 1 - Nov 2
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

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"The bed was very comfortable. The"
Angela 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Saugerties
Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

10/10 Excellent
"The room was very clean and the staff very helpful and courteous. May I suggest more table space in the rooms so that my luggage could be more manageable. This would help with my disability when unpacking. My handicap room was very helpful in maneuvering with the spacious bathroom. Thanks for a pleasant stay."
Mark 1-night trip
Posted 5 days ago
Spark by Hilton West Coxsackie

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 $89 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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