Find Hotels with a Pool in Windham, NY

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Check availability on Windham Hotels with a Pool

Check prices for these dates

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Windham Hotels with a Pool

The Colonial Motel
Relax by the pool surrounded by lounge chairs and umbrellas.

The Colonial Motel

2.5 star property
9.4 out of 10, Exceptional, (383)
"Great place!"
$99 nightly
The price is $109
Aug 6 - Aug 7
Total includes taxes and fees
The Colonial Motel
Hotel Vienna
Relax by the pool surrounded by comfortable loungers and chairs in a clean, minimalist space.

Hotel Vienna

2.5 star property
9.4 out of 10, Exceptional, (604)
"good place to stay at"
$124 nightly
The price is $134
Sep 4 - Sep 5
Total includes taxes and fees
Hotel Vienna
Shandaken Inn
Relax by the pool surrounded by lush greenery and a serene landscape.

Shandaken Inn

4.0 star property
10.0 out of 10, Exceptional, (257)
"This is a charming place to stay with beautiful views, great food and a warm and welcoming staff."
$219 nightly
The price is $245
Sep 1 - Sep 2
Total includes taxes and fees
Shandaken Inn
The Roxbury
Seasonal outdoor pool, sun loungers

The Roxbury

3.0 star property
9.6 out of 10, Exceptional, (117)
"Great stuff and location."
$154 nightly
The price is $168
Aug 11 - Aug 12
Total includes taxes and fees
The Roxbury
Winwood Condominiums by Windham Mountain Club
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Winwood Condominiums by Windham Mountain Club

3.0 star property
8.6 out of 10, Excellent, (328)
"Wonderful property "
$199 nightly
The price is $215
Aug 6 - Aug 7
Total includes taxes and fees
Winwood Condominiums by Windham Mountain Club
Wylder Hotel Windham
Relax by the serene pool surrounded by lush green hills and lounge under shaded umbrellas.

Wylder Hotel Windham

3.5 star property
8.6 out of 10, Excellent, (65)
"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend! "
$315 nightly
The price is $341
Aug 31 - Sep 1
Total includes taxes and fees
Wylder Hotel Windham
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski
Outdoor pool, a heated pool

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski

10.0 out of 10, Exceptional, (2)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
$1,473 nightly
The price is $1,591
Aug 11 - Aug 12
Total includes taxes and fees
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski
Condo in Windham Mountain Village
Stunning two-story home with a symmetrical facade, featuring a sloped roof and skylights.

Condo in Windham Mountain Village

10.0 out of 10, Exceptional, (12)
"Condo was clean and comfortable and very convenient to indoor pool and skiing. Thank you for a great vacation!"
$603 nightly
The price is $651
Aug 10 - Aug 11
Total includes taxes and fees
Condo in Windham Mountain Village
Charming Yacht on Catskill Creek
Compact kitchen area with microwave, refrigerator, sink, and window.

Charming Yacht on Catskill Creek

9.8 out of 10, Exceptional, (7)
"We had a nice night on the boat. Melissa was friendly and very nice. Made sure we had everything we needed. Place was clean to stay in. We had a relaxing night."
$207 nightly
The price is $223
Aug 11 - Aug 12
Total includes taxes and fees
Charming Yacht on Catskill Creek
Howard Johnson by Wyndham Saugerties
Relax by the pool surrounded by lush greenery and a geometric ceiling design.

Howard Johnson by Wyndham Saugerties

2.0 star property
7.6 out of 10, Good, (1007)
"Hotels, very nice and very clean"
$124 nightly
The price is $139
Aug 24 - Aug 25
Total includes taxes and fees
Howard Johnson by Wyndham Saugerties
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.

Top Windham Hotel Reviews

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"Super convenient to the horse show grounds and the staff was nice."
Jennifer 4-night trip
Posted 20 hours ago
Howard Johnson by Wyndham Saugerties

Frequently asked questions

What's it like visiting Windham?
If relaxing by the pool is your idea of a great vacation, you may want to consider relaxing Windham, which has 6 places to stay with pools. While you're here, you can explore attractions like Hunter Mountain, and then take it easy poolside at one of the accommodations in Windham that travelers like for their pools.
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. Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool, and complimentary bicycles. Eastwind Windham: Hotel located near Windham Mountain Resort. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Winwood Condominiums by Windham Mountain Club: Features a sauna, an indoor pool, and free self parking. Albergo Allegria Hotel & Breakfast Restaurant: Hotel, 13-minute walk from Hunter Mountain. Offers a sauna, an outdoor pool, and complimentary wireless internet access.
How many hotels with pools will I be able to find in Windham?
Expedia has 6 hotels in Windham for your poolside break.
What is there to see and do in Windham?
Explore places like Hunter Mountain while you're in the area. Take in the natural beauty with a stop at Ashland 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.