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

Top of the World! Jacuzzi! Private Hiking Trails!

Macintosh Hill Farm

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Okemo Ski Chalet with Hot Tub

Killington area home - 4-seasons & hot tub

Okemo-Ludlow, fireplace, hottub, sleeps 13

Killington ski house winter MTbike -new jacuzzi

Ski Chalet with Hot Tub on Okemo Mountain
Family- and pet-friendly home rentals

The Cozy Little Red Cabin

Vermont Chalet

Quiet Vermont Farmhouse

The McKinley House

The Guest House at Sky Hollow

Mountain Home ready for you!

The Green Mountain Chalet

"Downtown" Norwich Apartment
Family-friendly home rentals with a pool

Right at Killington !

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

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

One Bedroom Suite Near Okemo

*Killington Summer Rental: 3 Bdrm, 2 Bth*

Ski, Ride, Walk On/Off Condo On Pico at Killington

Serene Top Floor Condo (resort style amenities)

Modern Killington Farmhouse Condo: Close to Resort
Destinations to explore
- Cabin rentals Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Tenney Mountain Resort
- Northeast Slopes Ski Tow
- Dartmouth Skiway
- Dorset Field Club
- Ekwanok Country Club
- Hildene, The Lincoln Family Home
- Brattleboro Ski Hill
- Bretwood Golf Course
- Hooper Golf Course
- Autumn Mountain Winery
- Cozy Cottages & Otter Valley Winery
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Fox Run Golf Club
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes