A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Check availability on Windham Family Hotels

Our top choices for Windham family-friendly hotels

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 ₩231,704
₩250,240 total
includes taxes & fees
Nov 23 - Nov 24
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 ₩198,032
₩213,874 total
includes taxes & fees
Nov 15 - Nov 16
Jimmy OConnors Windham Mountain Inn
A two-story house with a wrap-around porch, a steeply pitched roof, and a small tower-like structure on the roof.

3. 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 ₩180,029
₩194,431 total
includes taxes & fees
Nov 16 - Nov 17
Antique Rose Inn Windham
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

4. 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 ₩264,223
₩352,039 total
includes taxes & fees
Nov 23 - Nov 24
Wylder Hotel Windham
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

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 ₩225,370
₩243,400 total
includes taxes & fees
Nov 15 - Nov 16
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 ₩194,431
₩410,004 total
includes taxes & fees
Nov 16 - Nov 17
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 family-friendly hotels in Windham

Breakfast included
Pool

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Relaxing getaway surrounded by nature. I enjoyed the sauna and pool each night. Would recommend for a relaxing solo trip!"
Shannon 3-night trip
Posted 4 hours ago
Hotel Vienna

Frequently asked questions

What's Windham like for family-friendly vacations?
The relaxing destination of Windham is a great choice if you've been considering a vacation with the kids. The golfing, coffee shops, and hiking trails are just a few things that make this an attractive spot for a family vacation. Take to the air and fly into Hudson, NY (HCC-Columbia County), which is located 27.6 mi (44.4 km) from the city center.
What's the best accommodation for families in Windham?
Wylder Hotel Windham is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Windham?
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.
What's there to see and do with your family in Windham?
While you are visiting Windham, you might want to round up the kiddos and make time to see interesting attractions such as Windham Mountain Resort, Zoom Flume, and Hunter Mountain. Make sure you have lots of time for activities like Kaaterskill Falls and Indian Head Mountain.