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
Home in Plymouth
4.95 out of 5 average rating, 237 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Chalet in Killington
4.83 out of 5 average rating, 235 reviewsKillington Chalet - Hot Tub, Sauna, Boot Dryer
Chalet in Ludlow
4.95 out of 5 average rating, 118 reviewsOkemo Ski Chalet with Hot Tub
Home in Pittsfield
4.84 out of 5 average rating, 227 reviewsKillington area home - 4-seasons & hot tub
Home in Cavendish
4.84 out of 5 average rating, 141 reviewsOkemo-Ludlow, fireplace, hottub, sleeps 13
Chalet in Stockbridge
4.93 out of 5 average rating, 175 reviewsKillington ski house winter MTbike -new jacuzzi
Chalet in Killington
4.87 out of 5 average rating, 242 reviewsLarge Chalet; Sauna, Hot Tub; Walk to Trail
Home in Ludlow
4.97 out of 5 average rating, 151 reviewsSki Chalet with Hot Tub on Okemo Mountain
Family- and pet-friendly home rentals
Cabin in Mount Holly
4.91 out of 5 average rating, 186 reviewsCozy Vermont Cabin near Okemo.
Rental unit in Springfield
4.95 out of 5 average rating, 151 reviewsConnecticut River Odyssey
Cabin in Woodstock
4.95 out of 5 average rating, 198 reviewsHideaway Cabin by the Stream on 27 Acres
Rental unit in Ludlow
4.92 out of 5 average rating, 262 reviewsOkemo Vermont Getaway
Home in Rochester
4.95 out of 5 average rating, 186 reviewsThe McKinley House
Home in Rochester
4.9 out of 5 average rating, 289 reviewsMountain Home ready for you!
Home in Rochester
4.97 out of 5 average rating, 197 reviewsThe Guest House at Sky Hollow
Cabin in Andover
4.96 out of 5 average rating, 165 reviewsSunrise Cabin
Family-friendly home rentals with a pool
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
Condo in Killington
4.82 out of 5 average rating, 251 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Killington
4.88 out of 5 average rating, 154 reviewsModern Killington Farmhouse Condo: Close to Resort
Condo in Killington
4.78 out of 5 average rating, 287 reviewsSerene Top Floor Condo (resort style amenities)
Condo in Killington
4.96 out of 5 average rating, 128 reviews#45 Luxury Ski & Summer Condo with Private Sauna
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Condo in Killington
4.93 out of 5 average rating, 415 reviewsPICO open Turkey week 1 bedroom 1 nite Ok shuttle
Condo in Killington
4.86 out of 5 average rating, 112 reviewsMountain Retreat: 4 Bdrm/2 Bath, Ski In, Bus Out
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