
Family-friendly holiday rentals in Windham
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham family-friendly rentals
Family-friendly home rentals with a hot tub

Greenville Getaway:HotTub&GameRoom.Cls toWaterPark

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

Mountain View Chalet: AC, Hot Tub, Firepit, Games

The Barnhouse - Ski House near Hunter and Windham

Stunning Cabin, Sauna, HT, MtnView, Mins 2 Windham

Red Fox TH mini golf path to pond & BBQ & hot tub

Wow! Panoramic Mountain View, Minutes to Windham!

Private Catskill Getaway | HotTub Mountain Views
Family- and pet-friendly home rentals

Windham Condo

"Your Country Getaway at Beulah Land Farm."
Woodstock Historic Artist Estate - The Pond House

Mtn Views • Firepit • 5 Min to Hiking + Brewery

"Far from the Madding Crowd" Cozy Cabin Retreat

The Garden House - Private, Secluded, & Mt Views!

Private Waterfall Retreat on 10 acres

Serendipity Lake House on Lake Heloise
Family-friendly home rentals with a pool

Plunge Pool, Sauna, AC! Modern Mountain Escape

Sweet Farm Stay

Exclusive Pool, Mtn Views! Hike, Golf, Swim, Relax

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Thorne Hollow - Mountain Ski Getaway with HotTub

Country Cottage w/ HOT TUB & Views

Modern Upstate Cabin, near Rhinebeck NY

Camp Catskills: Heated Pool I Fire-Pit I Hot Tub
Quick stats about holiday rentals that are family-friendly in Windham
Total rentals
150 properties
Nightly prices starting at
£81 before taxes and fees
Total number of reviews
5.5K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Rentals with a patio Windham
- Rentals with a fireplace Windham
- Pet-friendly rentals Windham
- Ski-in/ski-out rentals Windham
- Apartment rentals Windham
- Rentals with a washing machine and dryer Windham
- Cottage rentals Windham
- Fitness-friendly rentals Windham
- Cabin rentals Windham
- House rentals Windham
- Rentals with a firepit Windham
- Rentals with pools Windham
- Chalet rentals Windham
- Townhouse rentals Windham
- Rentals with a hot tub Windham
- Rentals with outdoor seating Windham
- Family-friendly rentals Greene County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Hunter Mountain
- Glimmerglass State Park
- Minnewaska State Park Preserve
- Belleayre Mountain Ski Center
- The Kartrite Resort & Indoor Waterpark
- Howe Caverns
- Resorts World Catskills
- John Boyd Thacher State Park
- Zoom Flume
- Bash Bish Falls State Park
- Walkway Over the Hudson State Historic Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Windham Mountain
- Albany Center Gallery
- Hunter Mountain Resort
- Opus 40
- Huck Finn’s Playland, Albany
- Hancock Shaker Village
- Taconic State Park
- Pineridge Cross Country Ski Area
- Plattekill Mountain
- Thaddeus Hait Farm
- Berkshire Botanical Garden