
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

Skiing and Breweries! Mountain and river views!

Charming private cape house in Woodstock

Entire lake house to yourself. Great for groups

Stony Hill Haus in Pine Plains

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

Location! Super clean apt. 8 min walk to Hunter!

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

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

Studio 3 BEDS-SLEEP 4

Cozy Condo w/ Wood Burning Fireplace

Ski on/ Ski off Stylish Condo Hunter Mountain

Cozy & walking distance to cafés *spring avails*

Harmony Valley Home, bright & inviting 2-BR escape
Quick stats about holiday rentals that are kid-friendly in Windham
Total rentals
50 properties
Nightly prices starting at
€ 155 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
10 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
- Rentals with outdoor seating Windham
- Chalet rentals Windham
- Rentals with a firepit Windham
- Ski-in/ski-out rentals Windham
- Rentals with a hot tub Windham
- Townhouse rentals Windham
- House rentals Windham
- Apartment rentals Windham
- Rentals with a fireplace Windham
- Pet-friendly rentals Windham
- Family-friendly rentals Windham
- Rentals with pools Windham
- Rentals with a patio Windham
- Fitness-friendly rentals Windham
- Cabin rentals Windham
- Rentals with a washing machine and dryer 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
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- Holiday Apartments Australia
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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
- Albany Center Gallery
- Minnewaska State Park Preserve
- Taconic State Park
- The Kartrite Resort & Indoor Waterpark
- Opus 40
- Thaddeus Hait Farm
- Walkway Over the Hudson State Historic Park
- Resorts World Catskills
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Bear Pond Winery
- Plattekill Mountain
- Berkshire Botanical Garden
- Naumkeag
- Zoom Flume
- Butternut Ski Area and Tubing Center
- Hancock Shaker Village
- John Boyd Thacher State Park
- Peebles Island State Park
- Glimmerglass State Park
- National Baseball Hall of Fame and Museum