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
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Windham hotels with a pool

Indoor pool
Exterior
Exterior
Exterior

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
$144 nightly
$155 total
Oct 1 - Oct 2
Total with taxes and fees
Hotel Vienna
Pool
Living area
Exterior
Room

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
Sep 16 - Sep 17
Total with taxes and fees
The Winwood Condominiums
Pool
Bathroom
Exterior
Exterior

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
$347 nightly
$374 total
Sep 24 - Sep 25
Total with taxes and fees
Wylder Hotel Windham
Pool
Interior
Terrace/patio
Living area

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
Sep 13 - Sep 14
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Pool
Property grounds
Property grounds
Exterior

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
$606 nightly
$654 total
Sep 13 - Sep 14
Total with taxes and fees
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Living area
Room
Dining
Interior

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.
$735 nightly
$794 total
Sep 11 - Sep 12
Total with taxes and fees
Condo in Windham Mountain Village
Pool
Dining
Terrace/patio
Living area

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.
$1,634 nightly
$1,764 total
Sep 13 - Sep 14
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Outdoor pool
Exterior
Exterior
Property entrance

8. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
$79 nightly
$87 total
Oct 6 - Oct 7
Total with taxes and fees
The Colonial Motel
Outdoor pool
Meeting facility
Room, 2 Double Beds
Porch

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.
$120 nightly
$130 total
Sep 11 - Sep 12
Total with taxes and fees
Moore's Motel
Pool
Exterior
Exterior
Living area

10. 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.
$208 nightly
$225 total
Sep 21 - Sep 22
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
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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 vacationed and traveled for 11 days and stayed at 10 different hotels in upstate NY. This hotel was the BEST. It was spacious, very clean, with an excellent breakfast. The host was polite, professional, and a lot of fun to visit with. We found an excellent place to wrap up with our sightseeing adventure. You will not be disappointed!!"
Don 1-night trip
Posted 2 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 $87 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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