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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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 10 - Nov 11
Total with taxes and fees
Albergo Allegria Hotel
A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.

2. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (910 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
$141 nightly
The price is $152
Nov 15 - Nov 16
Total with taxes and fees
Hotel Vienna
A sign for Cave Mountain Motel with a rustic stone wall and greenery.

3. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (152 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
$139 nightly
The price is $150
Nov 10 - Nov 11
Total with taxes and fees
Cave Mountain Motel
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

4. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
$276 nightly
The price is $297
Dec 10 - Dec 11
Total with taxes and fees
Eastwind Windham
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

5. 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
$147 nightly
The price is $159
Dec 10 - Dec 11
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.

6. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"Room super clean and beautiful property!"
United States
Daniela
$297 nightly
The price is $320
Dec 10 - Dec 11
Total with taxes and fees
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.

7. 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
$135 nightly
The price is $146
Nov 10 - Nov 11
Total with taxes and fees
Antique Rose Inn Windham
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

8. 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
$169 nightly
The price is $183
Nov 10 - Nov 11
Total with taxes and fees
The Winwood Condominiums
A bedroom with a large window, a bed, and a view of a forest.

9. 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
$306 nightly
The price is $330
Nov 17 - Nov 18
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

8/10 Good
"We had an excellent stay. We primarily booked it because it had a sauna, which was down this weekend so it was a little disappointing. However the room was very clean, modern and up to date. The bed was comfortable, as were the pillows. Great location with good restaurant options near by."
JESSICA A 2-night trip
Posted 1 day ago
Hotel Vienna

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 $97 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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