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

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Check availability on Windham Hotels with a Pool

Our top choices for Windham hotels with a pool

A large, two-story house with multiple porches and string lights.

1. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (289 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is AED 638
AED 689 total
includes taxes & fees
15 Nov - 16 Nov
Albergo Allegria Hotel
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

2. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.2 out of 10, Wonderful, (10 reviews)
"We had a wedding in the area and this place was perfect for our needs. There’s a bar to the front of the property, which was fun to hang out and play pool. The beds were comfortable and the rooms were clean."
United States
Robin
The price is AED 545
AED 589 total
includes taxes & fees
15 Nov - 16 Nov
Jimmy OConnors Windham Mountain Inn
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

3. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (139 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is AED 684
AED 922 total
includes taxes & fees
23 Nov - 24 Nov
Wylder Hotel Windham
A two-story house with a wrap-around porch, a steeply pitched roof, and a small tower-like structure on the roof.

4. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"A fantastic stay!"
United States
David
The price is AED 496
AED 536 total
includes taxes & fees
16 Nov - 17 Nov
Antique Rose Inn Windham
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

5. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (377 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is AED 621
AED 670 total
includes taxes & fees
15 Nov - 16 Nov
The Winwood Condominiums
A bedroom with a large window, a bed, and a view of a forest.

6. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
The price is AED 536
AED 1,129 total
includes taxes & fees
17 Nov - 18 Nov
The Haüs Windham
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Very clean, quiet AC, nice staff. Convenient location, easy to drive to nearby towns and hiking trails. À simple breakfast is included; good coffee all day. Quality of bedding and bath towels can be improved, but good enough for the price I paid."
Tianyu 3-night trip
Posted 7 hours ago
Hotel Vienna
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Comfortable beds"
Margaret 1-night trip
Posted 1 day 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. 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. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Jimmy OConnors Windham Mountain Inn: Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. The Haüs Windham: Hotel, 1-minute walk from Hunter Mountain. Provides 2 hot tubs, an outdoor pool, and a sauna.
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 Windham Vineyards and Winery. 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.