Find Family Hotels in Windham, NY

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Our top choices for Windham family-friendly hotels

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (731)
"Great service, nice and clean hotel."
United States
Mary
Hotel Vienna

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.8 out of 10, Excellent, (344)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is ¥29,600
¥31,967 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Winwood Condominiums by Windham Mountain Club

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.6 out of 10, Excellent, (89)
"Spotless room and great staff "
United States
Josue
The price is ¥33,418
¥43,921 total
includes taxes & fees
Dec 30 - Dec 31
Wylder Hotel Windham

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)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
The price is ¥131,206
¥254,997 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (14)
"Place was amazing "
United States
Erik B.
The price is ¥100,352
¥157,588 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Condo in Windham Mountain Village

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 ¥20,545
¥39,944 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Tiny House on Walnut Grove

Hanah mountain resort and country club

Hanah mountain resort and country club
2.0 star property
Margaretville
The price is ¥19,846
¥25,274 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hanah mountain resort and country club

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
7.8 out of 10, Good, (81)
"The service was excellent, very nice and helpful stuff and amazing atmosphere! Would definitely come back! "
United States
Kseniia
The price is ¥13,994
¥15,114 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spark by Hilton West Coxsackie

Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.2 out of 10, Very Good, (241)
"Great Stay would definitely recommend "
United States
Jay
The price is ¥23,329
¥26,128 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Catskill Seasons Inn

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1002)
"Easy check in, friendly staff. "
United States
Daniel
The price is ¥19,102
¥21,394 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Howard Johnson by Wyndham Saugerties
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.

Top Windham Hotel Reviews

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.