Find Hotels with a Pool in Windham, NY

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Check availability on Windham Hotels with a Pool

Tonight
Apr 28 - Apr 29
Tomorrow
Apr 29 - Apr 30
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

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, (799 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
$174 nightly
The price is $188
May 11 - May 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, (97 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
$279 nightly
The price is $302
May 8 - May 9
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
Apr 29 - Apr 30
Total with taxes and fees
Winwood Condominiums by Windham Mountain Club
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)
$467 nightly
The price is $504
Apr 29 - Apr 30
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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.
$733 nightly
The price is $792
Apr 29 - Apr 30
Total with taxes and fees
Condo in Windham Mountain Village
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.
$400 nightly
The price is $432
May 1 - May 2
Total with taxes and fees
The Outpost by Windham Mountain Club
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.
$1,386 nightly
The price is $1,496
Apr 29 - Apr 30
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Terrace/patio

The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.8 out of 10, Exceptional, (34 reviews)
  • cleanliness
    Splash into poolside fun at this Catskill Mountains motel, where seasonal swimming meets adventure in a charming outdoor oasis.
$144 nightly
The price is $161
Apr 29 - Apr 30
Total with taxes and fees
The Graham & Co.
Seasonal outdoor pool

Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (275 reviews)
  • cleanliness
    Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
$199 nightly
The price is $223
Apr 29 - Apr 30
Total with taxes and fees
Shandaken Inn
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, (439 reviews)
  • cleanliness
    Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
$89 nightly
The price is $98
Apr 30 - May 1
Total with taxes and fees
The Colonial Motel
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

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

2/10 Terrible
"There was a group out in the halls running around drinking and yelling ..till 2 30 in the morning..RUDE"
Steven 2-night trip
Posted 1 day ago
Howard Johnson by Wyndham Saugerties

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 $98 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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