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

Windham Hotel Guide - Family Friendly Hotels in Windham, New York

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Check availability on Windham Family Friendly Hotels

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Windham family-friendly hotels

A two-story building with a balcony, surrounded by well-maintained lawns and trees.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.
A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.
A view from a room with a glass door onto an outdoor patio. The patio has a metal table and two chairs, a small pumpkin decoration, and a metal fence.

1. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Fun family holidays await at Windham Mountain Club with seasonal pool, game room, and a short drive to skiing.
€163
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
A two-story building with large windows and a storefront.
A house with a snow-covered roof, surrounded by snow-laden trees and a mountainous backdrop.
A room with a view of a building and a body of water. There is a green chair and a lamp on a table.
A snow-covered tractor in a snowy landscape with trees.

2. 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
  • Create a cosy family ski retreat near Windham Mountain Resort with spacious rooms and convenient access to snow adventures.
€125
includes taxes & fees
1 Nov - 2 Nov
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A modern wooden cabin with a glass enclosure, surrounded by trees and a grassy area.
A wooden cabin with a balcony, surrounded by snow-covered trees.
A wooden cabin with a triangular roof, a wooden door, and a bench outside.
A bar area with wooden beams, a bar counter, and four bar stools.

3. Eastwind Windham

Eastwind Windham
Windham
€272
includes taxes & fees
25 Oct - 26 Oct
Eastwind Windham
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.

4. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into family fun near Windham Mountain Resort, where the outdoor pool and complimentary bicycles create adventures for all ages.
€303
includes taxes & fees
13 Oct - 14 Oct
Wylder Hotel Windham
A two-story building with large windows and a storefront.
A living room with a green sofa, two lamps, a small table with a keyboard, and three paintings on the wall.
A snow-covered tree with bare branches, a building with a blue facade, and a clear blue sky.
A house with a snow-covered roof, surrounded by snow-laden trees and a mountainous backdrop.

5. 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
  • Mountainside family retreat with kid-friendly amenities makes an easy walk to Windham's attractions and restaurants.
€207
includes taxes & fees
20 Oct - 21 Oct
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.
A spacious living area with a wooden staircase, a kitchen in the background, and a large window providing a view of the outdoors.
An indoor swimming pool area with a hot tub, seating, and a caution sign.
A spacious living area with a sectional sofa, a wooden coffee table, and a kitchen in the background.

6. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
€423
includes taxes & fees
3 Nov - 4 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A spacious living room with a stone fireplace, wooden staircase, and modern furniture.
A spacious living area with a wooden staircase, a stone fireplace, and a cozy seating arrangement.
A large, oval-shaped bathtub in a room with two large windows.
A modern bathroom with a glass-enclosed shower, a wooden vanity, and a marble floor.

7. Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace

Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace
Windham
€236
includes taxes & fees
3 Nov - 4 Nov
Duplex Suite with Marble Jacuzzi, Steam Shower and Gas Fireplace
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.
A modern living room with a staircase, green and beige sofas, a wooden coffee table, and a potted plant.
A living room with a green sofa, a yellow sofa, a coffee table with a bowl of fruit and a plant, a white chair, and a staircase in the background.
A hot tub with water, a house, and a tree with lights.

8. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
€520
includes taxes & fees
1 Nov - 2 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.
A snow-covered outdoor area with a table and chairs, surrounded by tall trees and a stack of firewood.
A living room with a sectional sofa, a coffee table, and a wooden ceiling.
A dining area with a table set for four, a vase with flowers, and a view of a forest through a large window with blinds.

9. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
€476
includes taxes & fees
2 Nov - 3 Nov
Pines Vignette • Modern 3BR Home in Windham
A fire pit with two chairs in a backyard.
A two-story house with a porch, a garage, and a driveway.
A modern living room with a sectional sofa, a coffee table, and a TV.
A bedroom with a wooden bed, a nightstand, a window with curtains, and a view of trees outside.

10. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
€555
includes taxes & fees
2 Nov - 3 Nov
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
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Choose what matters most at family-friendly hotels in Windham

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Windham Hotel Reviews

SunView Motel

SunView Motel

8/10 Good
"It was an awesome stay. Is what the website says"
Furquan 2-night trip
Posted 5 hours ago
SunView Motel
Hotel Vienna

Hotel Vienna

10/10 Excellent
"Hotel was clean, had pretty Catskills Mountains views, and fire pits, pool and sauna. Staff was helpful."
Glenn 1-night trip
Posted 17 hours ago
Hotel Vienna
Albergo Allegria Hotel

Albergo Allegria Hotel

10/10 Excellent
"What a find!! Impeccably clean. Beautiful Victorian architecture, super friendly and helpful owners. So many cozy nooks to hang out and relax. Restaurants within walking distance. I wish we came this way more often so I could stay again."
Staci 1-night trip
Posted 2 days ago
Albergo Allegria Hotel

Frequently asked questions

What's Windham like for family-friendly holidays?
The relaxing destination of Windham is a great choice if you've been considering a holiday with the children. The golf, coffee shops and hiking trails are just a few things that make this an attractive spot for a family holiday. Take to the air and fly into Hudson, NY (HCC-Columbia County), which is located 27.6 mi (44.4 km) from the city centre.
What's the best family accommodation 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 good option for your family trip.
When's the best time to book a family-friendly holiday in Windham?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do with your family in Windham?
While you are visiting Windham, you may want to round up the youngsters and make time to see interesting attractions such as Windham Mountain Resort, Zoom Flume and Hunter Mountain. Make sure that you have lots of time for activities such as Kaaterskill Falls and Indian Head Mountain.