Find Hotels with a Pool in Windham, NY

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Our top choices for Windham hotels with a pool

Indoor pool

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (801 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
$174 nightly
The price is $188
Jun 11 - Jun 12
Total with taxes and fees
Hotel Vienna
Outdoor pool

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (98 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
$306 nightly
The price is $331
May 25 - May 26
Total with taxes and fees
Wylder Hotel Windham
Seasonal outdoor pool

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.8 out of 10, Excellent, (353 reviews)
  • cleanliness
    Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
$159 nightly
The price is $172
May 21 - May 22
Total with taxes and fees
Winwood Condominiums by Windham Mountain Club
Indoor pool

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (7 reviews)
$468 nightly
The price is $505
Jun 3 - Jun 4
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Classic Double Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.4 out of 10, Very Good, (5 reviews)
  • cleanliness
    Alpine retreat near Windham Mountain offers free ski shuttle, seasonal outdoor pool, and slope-side relaxation.
$450 nightly
The price is $486
May 25 - May 26
Total with taxes and fees
The Outpost by Windham Mountain Club
Smart TV, fireplace

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (15 reviews)
  • cleanliness
    Mountain village condo offers ski-in/ski-out access, heated pool, and hot tub for year-round adventures.
$947 nightly
The price is $1,023
May 21 - May 22
Total with taxes and fees
Condo in Windham Mountain Village
Outdoor spa tub

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
10.0 out of 10, Exceptional, (7 reviews)
  • cleanliness
    Luxury mountain chalet offers year-round aquatic adventure with outdoor pool, hot tub, and water park.
$1,429 nightly
The price is $1,543
May 21 - May 22
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Exclusive House, Mountain View | Iron/ironing board, free WiFi

Red Feather Lodge

Red Feather Lodge
3.0 star property
Windham
$1,955 nightly
The price is $2,111
May 23 - May 24
Total with taxes and fees
Red Feather Lodge
Seasonal outdoor pool, pool umbrellas, sun loungers

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (442 reviews)
  • cleanliness
    Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
$78 nightly
The price is $86
Jun 9 - Jun 10
Total with taxes and fees
The Colonial Motel
Seasonal outdoor pool

Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (280 reviews)
  • cleanliness
    Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
$199 nightly
The price is $223
Jun 1 - Jun 2
Total with taxes and fees
Shandaken Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub

Top Windham Hotel Reviews

The Graham & Co.

The Graham & Co.

10/10 Excellent
"Loved the vibe!"
Barara 1-night trip
Posted 4 hours ago
The Graham & Co.

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 $86 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.
How can I save on a Windham hotel with a pool with Expedia?
Before booking your Windham hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
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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