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
Cabin in Windham
4.94 out of 5 average rating, 358 reviewsCozyCatskillChalet w/ Hot Tub (Catskill Mountains)
Aug 6 – 13
Home in Windham
4.87 out of 5 average rating, 126 reviewsLive the Slow Life at an All-Season Mountain Escape
May 12 – 19
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
May 16 – 23
Home in Jewett
4.96 out of 5 average rating, 156 reviewsLast minute deal! BBQ hut, She shed, Pizza oven
Aug 29 – Sep 5
Cottage in Phoenicia
4.89 out of 5 average rating, 800 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Jun 21 – 28
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
Dec 18 – 25
Home in Roxbury
4.99 out of 5 average rating, 224 reviewsCharming Cottage on 12 Secluded Acres + Hot Tub
May 31 – Jun 7
Chalet in Jewett
4.97 out of 5 average rating, 167 reviewsPrivate Renovated Catskills Home w. Hot Tub
May 10 – 17
Family- and pet-friendly home rentals
Tiny home in Shandaken
4.85 out of 5 average rating, 164 reviewsCute Cabin with Great Mountain Views
Jul 3 – 10
Home in Hunter
4.97 out of 5 average rating, 229 reviewsView Hunter mountain House
Sep 17 – 24
Tiny home in Roxbury
4.97 out of 5 average rating, 147 reviewsGlamping in New York the Catskills Birdhouse
Aug 25 – Sep 1
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Sep 23 – 30
Guesthouse in Woodstock
4.86 out of 5 average rating, 831 reviewsRocket Room - Rock Stars Only
Jan 12 – 19
Home in East Durham
4.92 out of 5 average rating, 223 reviewsBluff House
Mar 15 – 22
Cabin in Cornwallville
4.97 out of 5 average rating, 506 reviewsThe Log Cabin in the Catskills
Oct 3 – 10
Cabin in Andes
4.91 out of 5 average rating, 289 reviewsCabin in the Beautiful Catskills
Sep 8 – 15
Family-friendly home rentals with a pool
Home in Prattsville
4.91 out of 5 average rating, 125 reviewsLuxury Retreat in Lexington
May 29 – Jun 5
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 21 – 28
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Dec 4 – 11
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
May 17 – 24
Apartment in Earlton
4.93 out of 5 average rating, 279 reviewsSweet Farm Stay
Sep 22 – 29
Home in Hunter
4.92 out of 5 average rating, 158 reviewsCharming cabin with Hunter Mountain views
Jun 18 – 25
Guesthouse in Olivebridge
4.92 out of 5 average rating, 262 reviewsCozy Mountain Cottage With Saltwater Pool
Mar 8 – 15
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct 27 – Nov 3
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
R2,445 ZAR before taxes and fees
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