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, 282 reviewsSerene Killington Condo (resort style amenities)
Jul 4 – 11
Chalet in Killington
4.9 out of 5 average rating, 159 reviewsClose to Mountain and walk to restaurants!
Jul 1 – 8
Loft in Ludlow
4.95 out of 5 average rating, 735 reviewsSpacious Renovated Barn Apt on 100 acres!
Dec 31 – Jan 7
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Jul 10 – 17
Home in Killington
4.88 out of 5 average rating, 215 reviewsTanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ
May 31 – Jun 7
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Oct 4 – 11
Home in Plymouth
4.96 out of 5 average rating, 224 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
May 30 – Jun 6
Home in Wallingford
4.99 out of 5 average rating, 104 reviewsLuxury Mountain Retreat- Pond Hill Place
Oct 3 – 10
Family- and pet-friendly home rentals
Apartment in Woodstock
4.94 out of 5 average rating, 105 reviewsProspect Place
Jan 23 – 30
Cabin in Woodstock
4.96 out of 5 average rating, 191 reviewsCabin by the Stream on 27 Acres
Feb 15 – 22
Apartment in Springfield
4.91 out of 5 average rating, 222 reviewsFarm Barn apt. 3 bedr, 2 bath, fiberoptic internet
May 10 – 17
Cabin in Bethel
4.94 out of 5 average rating, 386 reviewsRustic and Cozy Vermont Getaway at Sugarwood Cabin
Apr 12 – 19
Cabin in West Windsor
4.97 out of 5 average rating, 127 reviewsCowshed Cabin Farm & Stable
Feb 28 – Mar 7
Home in Rochester
4.97 out of 5 average rating, 182 reviewsThe Guest House at Sky Hollow
Nov 11 – 18
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
Oct 8 – 15
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Sep 13 – 20
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
Sep 19 – 26
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
Aug 5 – 12
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Feb 19 – 26
Condo in Killington
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
Jun 5 – 12
Apartment in Killington
4.92 out of 5 average rating, 119 reviewsFamily and work friendly Spa at the Woods condo
Jul 30 – Aug 6
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
May 12 – 19
Condo in Killington
4.8 out of 5 average rating, 106 reviewsKillington Escape 2 Story 2BR 2BA Main Building
May 23 – 30
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsDana Road House Sunlit VT Country Home w/HotTub
Feb 3 – 10
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- Family-friendly rentals United States
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- Rentals with a fireplace Windsor County
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