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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
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Home in Plymouth
4.96 out of 5 average rating, 227 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
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Chalet in Killington
4.87 out of 5 average rating, 232 reviewsLarge Chalet; Sauna, Hot Tub; Walk to Trail
![](https://a0.muscache.com/im/pictures/hosting/Hosting-24499078/original/01cbcb09-45dd-4d08-8ddc-13b76c62469c.jpeg?im_w=720)
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
![](https://a0.muscache.com/im/pictures/50997721/d4767a5c_original.jpg?im_w=720)
Home in Ludlow
4.93 out of 5 average rating, 138 reviewsOKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!
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Home in Wallingford
4.99 out of 5 average rating, 104 reviewsLuxury Mountain Retreat- Pond Hill Place
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Chalet in Ludlow
4.97 out of 5 average rating, 116 reviewsOkemo Ski Chalet with Hot Tub
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Cabin in Sharon
4.92 out of 5 average rating, 250 reviewsCozy Cabin ‘birds nest’ off-grid seclusion
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Home in Pittsfield
4.83 out of 5 average rating, 222 reviewsKillington area home - 4-seasons & hot tub
Family- and pet-friendly home rentals
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Guest suite in Norwich
4.97 out of 5 average rating, 101 reviews"Downtown" Norwich Apartment
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Cabin in Mount Holly
4.9 out of 5 average rating, 186 reviewsCozy Vermont Cabin near Okemo.
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Rental unit in Ludlow
4.92 out of 5 average rating, 256 reviewsOkemo Vermont Getaway
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Home in Rochester
4.9 out of 5 average rating, 284 reviewsMountain Home ready for you!
![](https://a0.muscache.com/im/pictures/61485083/9d98b237_original.jpg?im_w=720)
Cabin in Andover
4.96 out of 5 average rating, 162 reviewsSunrise Cabin
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Home in Thetford
4.96 out of 5 average rating, 131 reviewsConnecticut River Summer Cottage
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Home in Rochester
4.95 out of 5 average rating, 182 reviewsThe McKinley House
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Chalet in Fairlee
4.91 out of 5 average rating, 497 reviewsThe Green Mountain Chalet
Family-friendly home rentals with a pool
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Apartment in Killington
4.8 out of 5 average rating, 235 reviewsCome to Killington this Summer!
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Apartment in Killington
4.89 out of 5 average rating, 235 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
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Apartment in Killington
4.77 out of 5 average rating, 284 reviewsSerene Killington Condo (resort style amenities)
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Apartment in Killington
4.96 out of 5 average rating, 121 reviews#45 Luxury Ski & Summer Condo with Private Sauna
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Apartment in Ludlow
4.8 out of 5 average rating, 152 reviewsEnjoy a Ski-On/Ski-Off Okemo Ski Getaway
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Apartment in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
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Rental unit in Killington
4.91 out of 5 average rating, 120 reviewsFamily and work friendly Spa at the Woods condo
![](https://a0.muscache.com/im/pictures/105928046/8e1abd29_original.jpg?im_w=720)
Apartment in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
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