
Family-friendly holiday 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.
Holiday 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

Okemo Ski Chalet with Hot Tub

Killington area home - 4-seasons & hot tub

Killington ski house winter MTbike -new jacuzzi

Large Chalet; Sauna, Hot Tub; Walk to Trail

Ski Chalet with Hot Tub on Okemo Mountain

Spacious Renovated Barn Apt on 100 acres!
Family- and pet-friendly home rentals

Cowshed Cabin Farm

The Cozy Little Red Cabin

Quiet Vermont Farmhouse

Vermont Chalet

The McKinley House

The Guest House at Sky Hollow

Mountain Home ready for you!

Sunrise Cabin
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

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

One Bedroom Suite Near Okemo

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

Serene Top Floor Condo (resort style amenities)
Destinations to explore
- Rentals with outdoor seating Windsor County
- Rentals with breakfast Windsor County
- Flat rentals Windsor County
- Rentals with a washing machine and dryer Windsor County
- Rentals with an accessible-height bed Windsor County
- Rentals with a firepit Windsor County
- Fitness-friendly rentals Windsor County
- Rentals with a hot tub Windsor County
- Beachfront rentals Windsor County
- Rentals with lake access Windsor County
- Bed and breakfasts Windsor County
- Farm stay rentals Windsor County
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- Chalet rentals Windsor County
- Rentals with an EV charger Windsor County
- Townhouse rentals Windsor County
- Rentals with a sauna Windsor County
- Waterfront rentals Windsor County
- Rentals with beach access Windsor County
- Rentals with a kayak Windsor County
- Ski-in/ski-out rentals Windsor County
- Guest house rentals Windsor County
- House rentals Windsor County
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- Villa rentals Windsor County
- Pet-friendly rentals Windsor County
- Family-friendly rentals Windsor County
- Cottage rentals Windsor County
- Apartment rentals Windsor County
- Rentals with pools Windsor County
- Tiny house rentals Windsor County
- Rentals with an accessible-height toilet Windsor County
- Rentals with a fireplace Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Fort Ticonderoga
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Dorset Field Club
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Bretwood Golf Course
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Mount Sunapee Resort
- Veterans Memorial Recreation Area Ski Hill
- Ekwanok Country Club
- Brattleboro Ski Hill
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Nature and outdoors Vermont
- Food and drink Vermont
- Things to do United States
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