
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

~The ClubHaus~

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Scandinavian design Chalet w/ private hiking trail

Renovated 1BR, Walk to Lifts, Covered parking

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

Blueberry Hill Escape | Pet Friendly | HotTub | Fi
Family- and pet-friendly home rentals

Convenient and chic private suite with 2 bedrooms!

The Cozy Little Red Cabin

Adorable one bedroom studio in 1844 farmhouse.

Hearth House Farm

Stock Farm Hideaway

The Guest House at Sky Hollow

Meadow View. 35 acres outside your door!

Addie's Place
Family-friendly home rentals with a pool

Renovated unit, prime location! Shuttle on/Ski off

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

Ranch at Mendon Mt Orchards

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

One Bedroom Suite Near Okemo

Newly renovated ski retreat at Killington

SKI ON/OFF Spruce Glen C | AC | Sauna| Fireplace

Serene Top Floor Condo (resort style amenities)
Destinations to explore
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Pet-friendly rentals Windsor County
- Fitness-friendly rentals Windsor County
- Rentals with lake access Windsor County
- Rentals with an EV charger Windsor County
- Rentals with pools Windsor County
- Rentals with outdoor seating Windsor County
- Rentals with an accessible-height bed Windsor County
- Flat rentals Windsor County
- Rentals with a hot tub Windsor County
- Farm stay rentals Windsor County
- Tiny house rentals Windsor County
- Rentals with a firepit Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with a kayak Windsor County
- Rentals with a washing machine and dryer Windsor County
- Beachfront rentals Windsor County
- Guest house rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Cottage rentals Windsor County
- Apartment rentals Windsor County
- Rentals with an accessible-height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with a sauna Windsor County
- Rentals with breakfast Windsor County
- Waterfront rentals Windsor County
- Villa rentals Windsor County
- Bed and breakfasts Windsor County
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- Rentals with a patio Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Tenney Mountain Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Stratton Mountain Resort
- Dorset Field Club
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Hooper Golf Course
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Lucky Bugger Vineyard & Winery
- Ekwanok Country Club
- Fox Run Golf Club
- Autumn Mountain Winery
- Whaleback Mountain
- Montshire Museum of Science
- Northeast Slopes Ski Tow
- Mount Sunapee Resort
- 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
- Tours United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Wellness United States
- Food and drink United States
- Sightseeing United States
- Art and culture United States