Family-friendly vacation rentals in Stockbridge
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Stockbridge
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 Stockbridge family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Pittsfield
4.83 out of 5 average rating, 221 reviewsKillington area home - 4-seasons & hot tub
Nov 1 – 8
Yurt in Randolph
4.96 out of 5 average rating, 386 reviews4 Season Lower Yurt Stay on VT Homestead
Oct 11 – 18
Condo in Killington
4.77 out of 5 average rating, 283 reviewsSerene Killington Condo (resort style amenities)
Jul 24 – 31
Chalet in Killington
4.9 out of 5 average rating, 159 reviewsClose to Mountain and walk to restaurants!
Jul 1 – 8
Home in Killington
4.88 out of 5 average rating, 215 reviewsTanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ
May 14 – 21
Chalet in Killington
5.0 out of 5 average rating, 117 reviewsLuxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard
Oct 29 – Nov 5
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Aug 29 – Sep 5
Chalet in Killington
4.82 out of 5 average rating, 234 reviewsKillington Chalet - Hot Tub, Sauna, Boot Dryer
Feb 13 – 20
Family- and pet-friendly home rentals
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
Nov 22 – 29
Cottage in Lincoln
4.87 out of 5 average rating, 857 reviewsThe Barn at North Orchard, Near Middlebury
Dec 9 – 16
Cottage in Brandon
4.91 out of 5 average rating, 266 reviewsHenrietta’s Hideaway-Walk Downtown!
Jan 24 – 31
Guesthouse in Granville
4.9 out of 5 average rating, 786 reviewsMoon Valley Country Retreat no clean fee pets yes
Dec 6 – 13
Home in Rochester
4.9 out of 5 average rating, 282 reviewsMountain Home ready for you!
Sep 16 – 23
Guesthouse in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
Aug 3 – 10
Cabin in Woodstock
4.96 out of 5 average rating, 191 reviewsCabin by the Stream on 27 Acres
Mar 3 – 10
Apartment in Andover
4.98 out of 5 average rating, 386 reviewsPrivate Hilltop farm apartment
Sep 29 – Oct 6
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
Jul 1 – 8
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
Aug 20 – 27
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Apr 17 – 24
Cabin in Bridport
4.92 out of 5 average rating, 133 reviewsChamplain Valley Alpacas
Oct 12 – 19
Apartment in Barre
4.94 out of 5 average rating, 156 reviewsRelax in Recreation Paradise!
Sep 10 – 17
Apartment in Killington
4.92 out of 5 average rating, 119 reviewsFamily and work friendly Spa at the Woods condo
Aug 2 – 9
Condo in Killington
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
Sep 12 – 19
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Apr 16 – 23
Quick stats about vacation rentals that are family-friendly in Stockbridge
Total rentals
80 properties
Wifi availability
80 properties include access to wifi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Total number of reviews
3.4K reviews
Nightly prices starting at
€ 103 before taxes and fees
Destinations to explore
- Burlington Vacation rentals
- Lake George Vacation rentals
- Lake Placid Vacation rentals
- Stowe Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Vermont
- Family-friendly rentals Vermont
- Family-friendly rentals New York
- Family-friendly rentals New Hampshire
- Rentals with a fire pit Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a fireplace Stockbridge
- House rentals Stockbridge
- Rentals with a patio Stockbridge
- Pet-friendly rentals Stockbridge
- Rentals with a washer and dryer Stockbridge
- Kid-friendly rentals Stockbridge
- Monthly Rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Family-friendly rentals Windsor County
- 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