Family-friendly holiday 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.
Holiday 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
25 Jan – 1 Feb
Cottage in Shaftsbury
4.99 out of 5 average rating, 599 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
13–20 Apr
Home in Newfane
4.97 out of 5 average rating, 114 reviewsPeaceful cabin close to skiing & Brattleboro
9–16 Jan
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
10–17 Jul
Loft in Ludlow
4.95 out of 5 average rating, 735 reviewsSpacious Renovated Barn Apt on 100 acres!
31 Dec – 7 Jan
Home in Lempster
4.88 out of 5 average rating, 367 reviewsDreamy lakefront cottage with views to die for!
11–16 Apr
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
6–13 Sept
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
22–29 Dec
Family- and pet-friendly home rentals
Flat in Town of Rockingham
4.82 out of 5 average rating, 159 reviewsApartment on Main Street
8–15 Oct
Tiny home in Jamaica
4.94 out of 5 average rating, 1143 reviewsApple Blossom Cottage: A Tiny House
3–10 Oct
Home in Grafton
4.97 out of 5 average rating, 130 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
5–12 Aug
Guest house in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
2–9 Jul
Cabin in Brattleboro
4.89 out of 5 average rating, 442 reviewsCottage
3–10 Jul
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
17–24 Jun
Flat in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
14–21 Feb
Cabin in Jamaica
4.88 out of 5 average rating, 264 reviewsGreen Mountain Modern House: iconic modern getaway
6–13 Mar
Family-friendly home rentals with a pool
Guest house in Granville
4.9 out of 5 average rating, 785 reviewsMoon Valley Country Retreat no clean fee pets yes
14–21 Dec
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
4–11 Dec
Home in Wilmington
4.9 out of 5 average rating, 130 reviews4 bedroom Ski House 15 min to Mount Snow
12–19 Jan
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
8–15 Sept
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
10–17 Feb
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
12–19 Apr
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
28 May – 4 Jun
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
13–20 Nov
Quick stats about holiday 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
£88 before taxes and fees
Destinations to explore
- Cambridge Holiday rentals
- Burlington Holiday rentals
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- Lake Placid Holiday rentals
- Philadelphia Holiday rentals
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