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
Loft in Ludlow
4.95 out of 5 average rating, 736 reviewsSpacious Renovated Barn Apt on 100 acres!
Condo in Killington
4.77 out of 5 average rating, 283 reviewsSerene Killington Condo (resort style amenities)
Home in Plymouth
4.96 out of 5 average rating, 225 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Chalet in Killington
5.0 out of 5 average rating, 117 reviewsLuxury, AC, 6 BR, 12 Bed, 3 Bath, Hot Tub,discount
Cabin in Sharon
4.92 out of 5 average rating, 246 reviewsCozy Cabin ‘birds nest’ off-grid seclusion
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Home in Pittsfield
4.83 out of 5 average rating, 221 reviewsKillington area home - 4-seasons & hot tub
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 Hancock
4.97 out of 5 average rating, 345 reviewsFunky, family-friendly cabin
Cabin in West Windsor
4.97 out of 5 average rating, 127 reviewsCowshed Cabin Farm & Stable
Apartment in Woodstock
4.94 out of 5 average rating, 105 reviewsProspect Place
Home in Rochester
4.97 out of 5 average rating, 183 reviewsThe Guest House at Sky Hollow
Apartment in Springfield
4.91 out of 5 average rating, 223 reviewsFarm Barn apt. 3 bedr, 2 bath, fiberoptic internet
Cabin in Bethel
4.94 out of 5 average rating, 391 reviewsRustic and Cozy Vermont Getaway at Sugarwood Cabin
Home in Weston
4.95 out of 5 average rating, 229 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Family-friendly home rentals with a pool
Condo in Killington
4.92 out of 5 average rating, 392 reviewsBike Golf Hike Pico 1 bedroom 1 night Ok shuttle
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
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Ludlow
4.8 out of 5 average rating, 149 reviewsEnjoy a Ski-On/Ski-Off Okemo Ski Getaway
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
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Vermont
- Family-friendly rentals Vermont
- Family-friendly rentals New York
- Family-friendly rentals New Hampshire
- Beachfront rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Pet-friendly rentals Windsor County
- Rentals with pools Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Rentals with an EV charger Windsor County
- Condo rentals Windsor County
- Cottage rentals Windsor County
- Rentals with outdoor seating Windsor County
- Apartment rentals Windsor County
- Bed and breakfasts Windsor County
- Ski-in/ski-out rentals Windsor County
- Farmstay rentals Windsor County
- Rentals with beach access Windsor County
- Rentals with breakfast Windsor County
- Rentals with lake access Windsor County
- Tiny house rentals Windsor County
- Fitness-friendly rentals Windsor County
- Rentals with a sauna Windsor County
- Townhouse rentals Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Rentals with a patio Windsor County
- Rentals with an accessible height bed Windsor County
- Kid-friendly rentals Windsor County
- Rentals with a fire pit Windsor County
- Monthly Rentals Windsor County
- Waterfront rentals Windsor County
- Villa rentals Windsor County
- Rentals with a hot tub Windsor County
- Rentals with a kayak Windsor County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes