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
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Popular amenities for Windsor County family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Killington
4.77 out of 5 average rating, 283 reviewsSerene Killington Condo (resort style amenities)
Loft in Ludlow
4.95 out of 5 average rating, 736 reviewsSpacious Renovated Barn Apt on 100 acres!
Chalet in Killington
4.9 out of 5 average rating, 159 reviewsClose to Mountain and walk to restaurants!
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Chalet in Killington
4.87 out of 5 average rating, 228 reviewsLarge Chalet; Sauna, Hot Tub; Walk to Trail
Home in Plymouth
4.96 out of 5 average rating, 225 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Chalet in Killington
5.0 out of 5 average rating, 117 reviewsLuxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard
Family- and pet-friendly home rentals
Cabin in Woodstock
4.96 out of 5 average rating, 191 reviewsCabin by the Stream on 27 Acres
Home in Rochester
4.97 out of 5 average rating, 182 reviewsThe Guest House at Sky Hollow
Cabin in Bethel
4.94 out of 5 average rating, 387 reviewsRustic and Cozy Vermont Getaway at Sugarwood Cabin
Apartment in Woodstock
4.94 out of 5 average rating, 105 reviewsProspect Place
Cabin in West Windsor
4.97 out of 5 average rating, 127 reviewsCowshed Cabin Farm & Stable
Home in Weston
4.95 out of 5 average rating, 228 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
Apartment in Ludlow
4.92 out of 5 average rating, 255 reviewsOkemo Vermont Getaway
Family-friendly home rentals with a pool
Condo in Killington
4.92 out of 5 average rating, 392 reviewsApril open 1 bedroom 1 night Ok Free shuttle
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
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
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
Apartment in Killington
4.92 out of 5 average rating, 119 reviewsFamily and work friendly Spa at the Woods condo
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Condo in Killington
4.8 out of 5 average rating, 106 reviewsKillington Escape 2 Story 2BR 2BA Main Building
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsDana Road House Sunlit VT Country Home w/HotTub
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