Family-friendly vacation 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.
Vacation 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
Cottage in Phoenicia
4.89 out of 5 average rating, 811 reviewsRomantic hot tub cottage.Breweries/swimming nearby
Home in Round Top
4.96 out of 5 average rating, 164 reviewsEscape in the Catskills w/hottub
Home in Windham
4.95 out of 5 average rating, 105 reviewsCharming Home Lg/Mod Kit Hot Tub on Stream FirePit
Cabin in Prattsville
4.82 out of 5 average rating, 157 reviews6 acre w/SWIM pond w/boats & floats plus HOT TUB!
Home in Windham
4.87 out of 5 average rating, 127 reviewsLive the Slow Life at an All-Season Mountain Escape
Home in Jewett
4.96 out of 5 average rating, 156 reviewsLast minute deal! BBQ hut, She shed, Pizza oven
Home in Woodstock
4.94 out of 5 average rating, 885 reviews1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole
Chalet in Jewett
4.97 out of 5 average rating, 167 reviewsPrivate Renovated Catskills Home w. Hot Tub
Family- and pet-friendly home rentals
Cabin in Gilboa
4.85 out of 5 average rating, 140 reviews🌟Cozy Cabin-Catskills secluded Mountain retreat🌟
Townhouse in Hunter
4.91 out of 5 average rating, 137 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
Tiny home in Shandaken
4.85 out of 5 average rating, 166 reviewsCute Cabin with Great Mountain Views
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 589 reviewsMagic Forest Farm's Mountain View Suite
Tiny home in Roxbury
4.97 out of 5 average rating, 154 reviewsGlamping in New York the Catskills Birdhouse
Cabin in Prattsville
4.82 out of 5 average rating, 102 reviewsCabin by a Stream
Cabin in Cornwallville
4.97 out of 5 average rating, 508 reviewsThe Log Cabin in the Catskills
Cottage in West Kill
4.97 out of 5 average rating, 257 reviewsCatskills Mountain Creek Cottage
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 273 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in woodstock
4.86 out of 5 average rating, 488 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio & Pool w/Deck Mountain Views
Guesthouse in Olivebridge
4.92 out of 5 average rating, 262 reviewsCozy Mountain Cottage With Saltwater Pool
Cabin in Saugerties
4.99 out of 5 average rating, 124 reviewsLovely cabin by the stream
Home in Hunter
4.92 out of 5 average rating, 158 reviewsCharming cabin with Hunter Mountain views
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Woodstock
4.96 out of 5 average rating, 107 reviewsWoodstock Modern Gem, Glorious Heated Saline Pool
Quick stats about vacation rentals that are family-friendly in Windham
Total rentals
150 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
50 properties allow pets
Total number of reviews
4.8K reviews
Nightly prices starting at
$130 before taxes and fees
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