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Check availability on Windham Family Hotels

Top Windham Family Hotels

The Windham Mountain View King with Balcony | In-room safe, iron/ironing board, free cribs/infant beds, rollaway beds
Wylder Hotel Windham

Wylder Hotel Windham

3.5 star property
Windham
8.8 out of 10, Excellent, (79)
"Everything was good"
United States
Laura Von
The price is ￥22,834
￥32,392 total
includes taxes & fees
Nov 16 - Nov 17
Wylder Hotel Windham
Exterior
Unwind Windham, Chalet

Unwind Windham, Chalet

Windham
10.0 out of 10, Exceptional, (2)
"We stayed only one night and we thought that should stay more nights because of the comfort of the house, the location, the amenities and the Property Host was there for answer any question. Definitely we come back now with the conviction that we have everything we need for an escape from New York city. I recommend this place in a 100% for sure. "
United States
Karla R.
The price is ￥19,991
￥80,600 total
includes taxes & fees
Nov 20 - Nov 21
Unwind Windham, Chalet
Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3.0 star property
Windham
8.8 out of 10, Excellent, (343)
"Great location and great property"
United States
Joel
The price is ￥26,132
￥28,223 total
includes taxes & fees
Nov 16 - Nov 17
Winwood Condominiums by Windham Mountain Club
Property grounds
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ashland
9.2 out of 10, Wonderful, (5)
"We really enjoyed staying here just because how relaxing it felt, to be outside enjoying the nice weather and having the horses run by. Just overall very soothing and quiet at night."
United States
Richard S.
The price is ￥31,563
￥57,300 total
includes taxes & fees
Nov 16 - Nov 17
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Terrace/patio
Drift Haus|4.5BR+ Mountain Lodge

Drift Haus|4.5BR+ Mountain Lodge

Windham
8.0 out of 10, Very Good, (1)
"The property was beautiful and peaceful. The kitchen was amazing and there were so many common areas that were great to socialize in. We did encounter some garbage left by the previous guests, but Will was responsive when we flagged it. There were a few repairs needed on the sliding doors, but overall it was a luxurious place to stay while we enjoyed the nature. "
United States
Grace H.
The price is ￥37,853
￥107,028 total
includes taxes & fees
Nov 17 - Nov 18
Drift Haus|4.5BR+ Mountain Lodge
Exterior
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

Ashland
The price is ￥47,645
￥81,515 total
includes taxes & fees
Nov 16 - Nov 17
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Fridge, microwave, oven, stovetop
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, (3)
"Everything was super "
United States
Hazal U.
The price is ￥110,097
￥225,785 total
includes taxes & fees
Nov 20 - Nov 21
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Exterior
Serene Catskills Escape: Hot Tub, Pond & Game Room

Serene Catskills Escape: Hot Tub, Pond & Game Room

Windham
10.0 out of 10, Exceptional, (16)
"The house is better than described. We had our annual extended family get together and more room than we needed. The adults and kids enjoyed the game rooms, hot tub movie room. The home was prepared with everything we needed. Very clean We will return. Beautiful home! "
United States
Suzanne n.
The price is ￥114,488
￥220,843 total
includes taxes & fees
Dec 1 - Dec 2
Serene Catskills Escape: Hot Tub, Pond & Game Room
Exterior
Condo in Windham Mountain Village

Condo in Windham Mountain Village

Windham
10.0 out of 10, Exceptional, (14)
"We had such a great stay at this home which was walking distance (even with little kids) to the mountain! The house was clean and very comfortable."
United States
Kristine M.
The price is ￥69,584
￥117,736 total
includes taxes & fees
Nov 16 - Nov 17
Condo in Windham Mountain Village
Terrace/patio
Tiny House on Walnut Grove

Tiny House on Walnut Grove

2.0 star property
Ashland
4.0 out of 10, (2)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
The price is ￥20,291
￥39,450 total
includes taxes & fees
Nov 16 - Nov 17
Tiny House on Walnut Grove
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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Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Room was nice and clean. The staff was beyond friendly and made me feel comfortable and welcomed. Would definitely stay here again!"
Jessica 2-night trip
Posted 6 days ago
Hotel Vienna

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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. Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge is another choice for your family trip.
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, Hunter Mountain, and Mountain Trails Cross Country Ski and Snowshoe Center. Make sure you have lots of time for activities like Kaaterskill Falls and Indian Head Mountain.