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
Condo in Killington
4.77 out of 5 average rating, 283 reviewsSerene Killington Condo (resort style amenities)
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Loft in Ludlow
4.95 out of 5 average rating, 735 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 Killington
4.89 out of 5 average rating, 273 reviewsKillington Mountain Retreat: Groups|Hot Tub|Games
Home in Plymouth
4.96 out of 5 average rating, 224 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Chalet in Killington
5.0 out of 5 average rating, 117 reviewsLuxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Family- and pet-friendly home rentals
Cabin in Woodstock
4.96 out of 5 average rating, 191 reviewsCabin by the Stream on 27 Acres
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
Home in Rochester
4.97 out of 5 average rating, 182 reviewsThe Guest House at Sky Hollow
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, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Apartment in Ludlow
4.92 out of 5 average rating, 255 reviewsOkemo Vermont Getaway
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
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.
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
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
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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