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
Home in Windham
4.87 out of 5 average rating, 127 reviewsLive the Slow Life at an All-Season Mountain Escape
Jul 18 – 25
Home in Jewett
4.96 out of 5 average rating, 156 reviewsLast minute deal! BBQ hut, She shed, Pizza oven
Mar 28 – Apr 4
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
May 28 – Jun 4
Chalet in Jewett
4.97 out of 5 average rating, 167 reviewsPrivate Renovated Catskills Home w. Hot Tub
May 16 – 23
Cottage in Phoenicia
4.89 out of 5 average rating, 804 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Sep 27 – Oct 4
Cabin in Saugerties
4.86 out of 5 average rating, 173 reviewsContainer Cabin in the Catskills (Field)
Sep 30 – Oct 7
Cabin in Prattsville
4.82 out of 5 average rating, 154 reviews6 acre w/SWIM pond w/boats & floats plus HOT TUB!
Oct 17 – 24
Home in Roxbury
4.99 out of 5 average rating, 225 reviewsCharming Cottage on 12 Secluded Acres + Hot Tub
Sep 2 – 9
Family- and pet-friendly home rentals
Home in Hunter
4.97 out of 5 average rating, 229 reviewsView Hunter mountain House
Aug 6 – 13
Home in East Durham
4.92 out of 5 average rating, 223 reviewsBluff House
Sep 17 – 24
Cabin in Cornwallville
4.97 out of 5 average rating, 507 reviewsThe Log Cabin in the Catskills
Oct 15 – 22
Tiny home in Shandaken
4.85 out of 5 average rating, 164 reviewsCute Cabin with Great Mountain Views
Jul 14 – 21
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 583 reviewsMagic Forest Farm's Mountain View Suite
Aug 28 – Sep 4
Tiny home in Roxbury
4.97 out of 5 average rating, 147 reviewsCatskills Birdhouse @bellfirefarm
Aug 27 – Sep 3
Guesthouse in Woodstock
4.86 out of 5 average rating, 831 reviewsRocket Room - Rock Stars Only
Jan 20 – 27
Cottage in West Kill
4.97 out of 5 average rating, 255 reviewsCatskills Mountain Creek Cottage
Jan 2 – 9
Family-friendly home rentals with a pool
Home in Prattsville
4.91 out of 5 average rating, 125 reviewsLuxury Retreat in Lexington
Sep 21 – 28
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Jan 28 – Feb 4
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 7 – 14
Apartment in Earlton
4.93 out of 5 average rating, 279 reviewsSweet Farm Stay
Oct 4 – 11
Home in Hunter
4.92 out of 5 average rating, 158 reviewsCharming cabin with Hunter Mountain views
May 21 – 28
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 10 – 17
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Sep 17 – 24
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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