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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Hotels with a Pool

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Windham hotels with a pool

Indoor pool
Exterior
Exterior
View from room

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
$164 nightly
$177 total
Sep 7 - Sep 8
Total with taxes and fees
Hotel Vienna
Seasonal outdoor pool
Living area
Living area
Exterior

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
Aug 17 - Aug 18
Total with taxes and fees
The Winwood Condominiums
Outdoor pool
Restaurant
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.
$300 nightly
$324 total
Aug 17 - Aug 18
Total with taxes and fees
Wylder Hotel Windham
Indoor pool
TV, fireplace
TV, fireplace
Interior

4. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
$522 nightly
$564 total
Sep 14 - Sep 15
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Smart TV, fireplace
Interior
Exterior
3 bedrooms, WiFi (free), bed sheets

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.
$959 nightly
$1,036 total
Aug 17 - Aug 18
Total with taxes and fees
Condo in Windham Mountain Village
Outdoor pool, a heated pool
Dining
Terrace/patio
Smart TV, fireplace, books, stereo

6. 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.
$1,652 nightly
$1,784 total
Aug 19 - Aug 20
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Outdoor pool
Porch
Room, 2 Double Beds | WiFi (free)
Porch

7. 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
Aug 17 - Aug 18
Total with taxes and fees
Moore's Motel
Seasonal outdoor pool, pool umbrellas, sun loungers
Exterior
Property entrance
Lobby sitting area

8. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
$88 nightly
$97 total
Aug 20 - Aug 21
Total with taxes and fees
The Colonial Motel
Outdoor pool
Exterior
Lobby
32-inch TV with cable channels

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.
$209 nightly
$229 total
Sep 16 - Sep 17
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
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

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 $97 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.

Explore a world of travel with Expedia