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, (763 reviews)
"Always stay here during the skies season."
United States
Benjamin
Hotel Vienna
Outdoor pool

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.6 out of 10, Excellent, (92 reviews)
"Very nice hotel. Exactly what we needed."
United States
Nicolas
The price is SAR 743
SAR 990 total
includes taxes & fees
1 Mar - 2 Mar
Wylder Hotel Windham
Seasonal outdoor pool

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.6 out of 10, Excellent, (350 reviews)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is SAR 746
SAR 806 total
includes taxes & fees
22 Feb - 23 Feb
Winwood Condominiums by Windham Mountain Club
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)
"Cozy and warm. I think it would be better to visit during the winter season"
United States
TAEJUN
The price is SAR 938
SAR 1,013 total
includes taxes & fees
22 Feb - 23 Feb
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, (14 reviews)
"Place was amazing "
United States
Erik B.
The price is SAR 2,494
SAR 3,836 total
includes taxes & fees
4 Mar - 5 Mar
Condo in Windham Mountain Village
Pool

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.4 out of 10, Exceptional, (3 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is SAR 957
SAR 2,212 total
includes taxes & fees
23 Mar - 24 Mar
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Outdoor spa tub

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Windham
10.0 out of 10, Exceptional, (4 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
The price is SAR 2,813
SAR 5,683 total
includes taxes & fees
23 Mar - 24 Mar
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
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, (423 reviews)
"Awesome place!"
United States
Richard
The price is SAR 334
SAR 368 total
includes taxes & fees
22 Feb - 23 Feb
The Colonial Motel
Terrace/patio

The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (24 reviews)
"This place was perfect for a quick hiking trip, very simple but has everything you need. Room was very comfy and clean. Would definitely stay here again! "
United States
Amanda
The price is SAR 540
SAR 605 total
includes taxes & fees
17 Mar - 18 Mar
The Graham & Co.
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

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Very clean, modern, great amenities. Breakfast croissants were excellent. Very friendly staff. We will definitely visit again. "
Seamus 1-night trip
Posted 7 days ago
Hotel Vienna

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. 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: Vacation home located near Windham Mountain Resort. Features kitchens, a pool, and televisions. Albergo Allegria Hotel & Breakfast Restaurant: Features buffet, an indoor pool, and free self parking.
What is there to see and do in Windham?
Explore places like Hunter Mountain while you're in the area. Spend some time experiencing the great outdoors at Ashland Park and Elm Ridge Wild Forest. 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.