
Kid-friendly holiday rentals in Windham
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Windham
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals

Perfect Family Retreat•Pool•Volleyball•Firepit

LOW Cleaning Fee! Family friendly with swing set

Hiking and Breweries! Mountain and river views!

Entire lake house to yourself. Great for groups

Stony Hill Haus in Pine Plains

A Perfect Upstate Family Getaway with a Pool

Sweeping mountain views in Woodstock, NY

Wooded Livingston Manor Oasis With Stream & Deck
Family-friendly apartment rentals

Mountain View Apartment

Lower Warren Street Picture-Perfect 2-Bedroom Apt

Chic Hudson Apartment - In the heart of Hudson, NY

Private 1BR Apartment 1 Block from Warren St.

2 bedroom / Office - HEPA Air Purifier

Above SpringRise

Woodland Neighborhood Retreat

Sunny, Spacious & Central: Bowler
Family-friendly apartment rentals

Trailside At Hunter-Phase II-Hunter NY

Cozy Mountain hideaway Windham, Hunter

Mint*Cozy*Ski In/Out*Hunter Mt Condo w/Fireplace

Windham-Hunter Lodge

Studio 3 BEDS-SLEEP 4

Summer Retreat w/ Balcony & inground Pool

Stylish Condo Hunter Mountain

Cozy & walking distance to cafés *spring avails*
Quick stats about holiday rentals that are kid-friendly in Windham
Total rentals
60 properties
Nightly prices starting at
€ 97 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- The Hamptons Holiday rentals
- Jersey Shore Holiday rentals
- Boston Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Cape Cod Holiday rentals
- Cabin rentals Windham
- Rentals with outdoor seating Windham
- Apartment rentals Windham
- Townhouse rentals Windham
- Rentals with pools Windham
- Ski-in/ski-out rentals Windham
- Rentals with a washing machine and dryer Windham
- Rentals with a hot tub Windham
- Rentals with a fireplace Windham
- Pet-friendly rentals Windham
- Rentals with a patio Windham
- Chalet rentals Windham
- Rentals with a firepit Windham
- Fitness-friendly rentals Windham
- House rentals Windham
- Family-friendly rentals Windham
- Family-friendly rentals Greene County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
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- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Holiday Apartments Australia
- Holiday Houses United States
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- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Albany Center Gallery
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Glimmerglass State Park
- John Boyd Thacher State Park
- Zoom Flume
- Opus 40
- Norman Rockwell Museum
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Naumkeag
- Thaddeus Hait Farm
- Huck Finn’s Playland, Albany
- Plattekill Mountain
- Peebles Island State Park
- Pineridge Cross Country Ski Area
- Berkshire Botanical Garden
- Hancock Shaker Village