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

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

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
$174 nightly
The price is $188
Nov 1 - Nov 2
Total with taxes and fees
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
$135 nightly
The price is $146
Nov 23 - Nov 24
Total with taxes and fees
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, (134 reviews)
"Loved our stay, will go anytime for a little weekend getaway from nyc!"
United States
Yassaman Modarres
$204 nightly
The price is $220
Nov 1 - Nov 2
Total with taxes and fees
Wylder Hotel Windham
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

4. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (372 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
$169 nightly
The price is $183
Nov 1 - Nov 2
Total with taxes and fees
The Winwood Condominiums
A bedroom with a large window, a bed, and a view of a forest.

5. 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
$314 nightly
The price is $340
Nov 2 - Nov 3
Total with taxes and fees
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
"We booked Hotel Vienna at the last moment and it turned out to be such a pleasant and beautiful stay. The location is simply mesmerizing and true treat to the eyes. We loved the walk behind the hotel which leads to a creek and meadow. It’s a hidden gem in Catskills. The staff ‘ Jessica’ was very nice and guided us to a lovely restaurant nearby. The breakfast is top notch . Fresh out of oven . Loved everything about our stay We will go back and recommend ."
Varsha 1-night trip
Posted 5 hours ago
Hotel Vienna
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Only stayed 1 night, but room was clean & comfortable. Would stay again in the future."
Frank 1-night trip
Posted 2 days 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 $89 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.
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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