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
Aug 23 – 30
Cottage in Shaftsbury
4.99 out of 5 average rating, 600 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Mar 6 – 13
Loft in Ludlow
4.95 out of 5 average rating, 735 reviewsSpacious Renovated Barn Apt on 100 acres!
Jun 4 – 11
Home in Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
Apr 12 – 19
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Mar 21 – 28
Home in Lempster
4.88 out of 5 average rating, 367 reviewsDreamy lakefront cottage with views to die for!
Dec 20 – 25
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
Nov 14 – 21
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
Dec 28 – Jan 4
Family- and pet-friendly home rentals
Home in Grafton
4.97 out of 5 average rating, 130 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
Oct 30 – Nov 6
Cabin in Brattleboro
4.89 out of 5 average rating, 443 reviewsCottage
Jul 9 – 16
Apartment in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
Nov 29 – Dec 6
Guesthouse in Granville
4.9 out of 5 average rating, 786 reviewsMoon Valley Country Retreat no clean fee pets yes
Jan 9 – 16
Cabin in Jamaica
4.88 out of 5 average rating, 265 reviewsGreen Mountain Modern House: iconic modern getaway
Mar 13 – 20
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
Aug 19 – 26
Guest suite in Mt Holly
4.98 out of 5 average rating, 117 reviewsExquisite Green Mountain Loft Haven
Sep 19 – 26
Apartment in Springfield
4.91 out of 5 average rating, 223 reviewsFarm Barn apt. 3 bedr, 2 bath, fiberoptic internet
May 30 – Jun 6
Family-friendly home rentals with a pool
Condo in Killington
4.92 out of 5 average rating, 392 reviewsApril open 1 bedroom 1 night Ok Free shuttle
Jun 25 – Jul 2
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 29 – Sep 5
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Jan 10 – 17
Condo in Ludlow
4.8 out of 5 average rating, 148 reviewsEnjoy a Ski-On/Ski-Off Okemo Ski Getaway
Apr 13 – 20
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Nov 13 – 20
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 30 – Feb 6
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Apr 7 – 14
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Nov 20 – 27
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
R2,035 ZAR before taxes and fees
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