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

Exterior

The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (354 reviews)
  • cleanliness
    Fun family vacations await at Windham Mountain Club with seasonal pool, game room, and a short drive to skiing.
The price is AED 559
AED 603 total
includes taxes & fees
22 Jun - 23 Jun
The Winwood Condominiums
Exterior

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (100 reviews)
  • cleanliness
    Splash into family fun near Windham Mountain Resort, where the outdoor pool and complimentary bicycles create adventures for all ages.
The price is AED 808
AED 1,057 total
includes taxes & fees
22 Jun - 23 Jun
Wylder Hotel Windham
Exterior

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
  • cleanliness
    Create a cozy family ski retreat near Windham Mountain Resort with spacious rooms and convenient access to snow adventures.
The price is AED 312
AED 536 total
includes taxes & fees
22 Jun - 23 Jun
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (60 reviews)
  • cleanliness
    Mountainside family retreat with kid-friendly amenities makes an easy walk to Windham's attractions and restaurants.
The price is AED 477
AED 801 total
includes taxes & fees
21 Jun - 22 Jun
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Interior

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (15 reviews)
The price is AED 1,570
AED 2,616 total
includes taxes & fees
21 Jun - 22 Jun
Condo in Windham Mountain Village
Bar (on property)

Howland House

Howland House
2.0 star property
Mount Tremper
9.8 out of 10, Exceptional, (6 reviews)
The price is AED 626
AED 702 total
includes taxes & fees
24 Jun - 25 Jun
Howland House
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
"The access to the Windam Path was great. It is a lovely, easy walk by a stream and through meadows."
Barbara 1-night trip
Posted 1 hour 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, Zoom Flume, and Hunter Mountain. Make sure you have lots of time for activities like Kaaterskill Falls and Indian Head Mountain.