
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

Guest house
4.96 out of 5 average rating, 255 reviewsMacintosh Hill Farm

Chalet
4.83 out of 5 average rating, 242 reviewsKillington Chalet - Hot Tub, Sauna, Boot Dryer

Home
4.82 out of 5 average rating, 11 reviews4 Bdrm house 5 min to skiing, hiking, golf, biking

Home
4.83 out of 5 average rating, 233 reviewsKillington area home - 4-seasons & hot tub

Townhouse
4.98 out of 5 average rating, 51 reviewsOkemo village/ Indoor private hot tub.

Home
4.87 out of 5 average rating, 85 reviewsThe Sundowner

Chalet
4.92 out of 5 average rating, 178 reviewsKillington ski house winter MTbike -new jacuzzi

Loft
4.95 out of 5 average rating, 792 reviewsSpacious Renovated Barn Apt on 100 acres!
Family- and pet-friendly home rentals

Home
4.87 out of 5 average rating, 186 reviews2 Doors Down - Modern Farmhouse in Downtown Ludlow

Home
4.95 out of 5 average rating, 245 reviewsTop of the World! Jacuzzi! Private Hiking Trails!

Cabin
4.95 out of 5 average rating, 152 reviewsThe Cozy Little Red Cabin

Cabin
4.95 out of 5 average rating, 198 reviewsHideaway Cabin by the Stream on 27 Acres

Cabin
4.95 out of 5 average rating, 244 reviewsHancock hideaway

Chalet
4.86 out of 5 average rating, 147 reviewsVermont Chalet

Home
4.78 out of 5 average rating, 104 reviewsSugarbush 1880s Farmhouse - With Scenic Views 5/2

Home
4.98 out of 5 average rating, 203 reviewsThe Guest House at Sky Hollow
Family-friendly home rentals with a pool

Guest suite
4.95 out of 5 average rating, 142 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.

Apartment
4.95 out of 5 average rating, 102 reviews⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Apartment
4.8 out of 5 average rating, 104 reviewsSki Mountain Escape: 3 Bdrm, Ski In & Bus In

Apartment
4.82 out of 5 average rating, 257 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington

Apartment
4.77 out of 5 average rating, 297 reviewsSerene Top Floor Condo (resort style amenities)

Apartment
4.96 out of 5 average rating, 137 reviews#45 Luxury Ski & Summer Condo with Private Sauna

Apartment
4.93 out of 5 average rating, 435 reviewsPico Ski in out 1 bedroom 1 nite Ok free shuttle

Apartment
4.97 out of 5 average rating, 143 reviews2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
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