
Family-friendly vacation rentals in Weston
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Weston
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 Weston family-friendly rentals
Family-friendly home rentals with a hot tub

Top of the World! Jacuzzi! Private Hiking Trails!

Okemo Ski Chalet with Hot Tub

Serene Top Floor Condo (resort style amenities)

Large Chalet; Sauna, Hot Tub; Walk to Trail

Peaceful cabin close to skiing & Brattleboro

Ski Chalet with Hot Tub on Okemo Mountain

Spacious Renovated Barn Apt on 100 acres!

Okemo Mountain Getaway for Families w/ Pool Access
Family- and pet-friendly home rentals

The King's Cottage

Cowshed Cabin Farm

The Cozy Little Red Cabin

1850's VT Farmhouse on the River

Mountain treasures await.

Yurt In The Woods - Private Refuge

Rock River Retreat: VT Oasis Pet Friendly

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!

Bear's Den - Mt Snow Townhome w/ Heated Pool!

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

Mt Snow Ski In/Out at Seasons

One Bedroom Suite Near Okemo

Modern Killington Farmhouse Condo: Close to Resort

Hike bike golf 1 bedroom 1 nght Ok shuttle

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
Quick stats about vacation rentals that are family-friendly in Weston
Total rentals
50 properties
Nightly prices starting at
G$27,168 GYD before taxes and fees
Total number of reviews
2.2K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
Destinations to explore
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- Rentals with a washer and dryer Weston
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- Family-friendly rentals Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Ragged Mountain Resort
- Lake George Expedition Park
- Fort Ticonderoga
- Dorset Field Club
- Autumn Mountain Winery
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Clarksburg State Park
- Ekwanok Country Club
- Bretwood Golf Course
- Brattleboro Ski Hill