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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Hotels with a Pool

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, (825 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
The price is ￥21,525
￥26,041 total
includes taxes & fees
Aug 9 - Aug 10
Hotel Vienna
Seasonal outdoor pool

The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (355 reviews)
  • cleanliness
    Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
The price is ￥26,061
￥28,147 total
includes taxes & fees
Jul 13 - Jul 14
The Winwood Condominiums
Outdoor pool

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (101 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
The price is ￥42,663
￥54,159 total
includes taxes & fees
Jul 28 - Jul 29
Wylder Hotel Windham
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.
The price is ￥107,517
￥164,137 total
includes taxes & fees
Jul 12 - Jul 13
Condo in Windham Mountain Village
Outdoor pool, a heated pool

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.
The price is ￥137,428
￥259,128 total
includes taxes & fees
Jul 13 - Jul 14
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Indoor pool, a heated pool

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
10.0 out of 10, Exceptional, (1 review)
The price is ￥72,756
￥108,785 total
includes taxes & fees
Jul 12 - Jul 13
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
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)
The price is ￥41,228
￥97,609 total
includes taxes & fees
Jul 14 - Jul 15
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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, (456 reviews)
  • cleanliness
    Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
The price is ￥14,405
￥15,847 total
includes taxes & fees
Jul 12 - Jul 13
The Colonial Motel
Outdoor pool

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (173 reviews)
  • cleanliness
    Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
The price is ￥19,402
￥20,954 total
includes taxes & fees
Jul 13 - Jul 14
Moore's 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.
View all properties

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

10/10 Excellent
"Excellent service and quick checking room was very clean"
John 1-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Saugerties

Frequently asked questions

What are some accommodations with pools in Windham?
Hotel Vienna: Hotel located near Windham Mountain Resort. Features daily, an indoor pool, and free self parking. Eastwind Windham: Hotel located near Windham Mountain Resort. Provides free self parking, a seasonal outdoor pool, and complimentary bicycles. Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Jimmy OConnors Windham Mountain Inn: Hotel located near Catskill Mountains. Provides a full-service spa, a seasonal outdoor pool, and complimentary bicycles. Albergo Allegria Hotel: Hotel located near HITS-on-the-Hudson. Features buffet, an indoor pool, and free self parking.
What is there to see and do in Windham?
Surround yourself with nature at Elm Ridge Wild Forest and Ashland Park. During your stay, check out sights such as Windham Country Club, Windham Mountain Resort, and Catskill State Park. The mountain views, skiing, and coffeehouses are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Windham?
Taking into account the local weather in Windham is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.