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 Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Jan 24 – 31
Cottage in Shaftsbury
4.99 out of 5 average rating, 598 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Feb 6 – 13
Loft in Ludlow
4.95 out of 5 average rating, 735 reviewsSpacious Renovated Barn Apt on 100 acres!
Apr 18 – 25
Home in Newfane
4.97 out of 5 average rating, 114 reviewsPeaceful cabin close to skiing & Brattleboro
Jan 9 – 16
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Aug 30 – Sep 6
Home in Wilmington
4.9 out of 5 average rating, 130 reviews4 bedroom Ski House 15 min to Mount Snow
May 15 – 22
Home in Lempster
4.88 out of 5 average rating, 367 reviewsDreamy lakefront cottage with views to die for!
Jan 14 – 19
Condo in Killington
4.77 out of 5 average rating, 282 reviewsSerene Killington Condo (resort style amenities)
Jul 4 – 11
Family- and pet-friendly home rentals
Apartment in Town of Rockingham
4.82 out of 5 average rating, 159 reviewsApartment on Main Street
Oct 8 – 15
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Aug 23 – 30
Tiny home in Jamaica
4.94 out of 5 average rating, 1143 reviewsApple Blossom Cottage: A Tiny House
Oct 3 – 10
Home in Grafton
4.97 out of 5 average rating, 130 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
Aug 31 – Sep 7
Guesthouse in Granville
4.9 out of 5 average rating, 785 reviewsMoon Valley Country Retreat no clean fee pets yes
Apr 16 – 23
Cabin in Brattleboro
4.89 out of 5 average rating, 442 reviewsCottage
Jun 11 – 18
Apartment in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
Jan 28 – Feb 4
Cabin in Jamaica
4.88 out of 5 average rating, 264 reviewsGreen Mountain Modern House: iconic modern getaway
Mar 6 – 13
Family-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Jan 3 – 10
Condo in Killington
4.92 out of 5 average rating, 392 reviewsApril open 1 bedroom 1 night Ok Free shuttle
Sep 19 – 26
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 8 – 15
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Apr 6 – 13
Condo in Ludlow
4.8 out of 5 average rating, 148 reviewsEnjoy a Ski-On/Ski-Off Okemo Ski Getaway
Apr 6 – 13
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Mar 8 – 15
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun 4
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Nov 13 – 20
Quick stats about vacation rentals that are family-friendly in Windham
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.4K reviews
Nightly prices starting at
G$22,952 GYD before taxes and fees
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