Family-friendly holiday 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.
Holiday 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
2–9 Nov
Apartment in Killington
4.77 out of 5 average rating, 283 reviewsSerene Killington Condo (resort style amenities)
17–24 Jul
Yurt in Randolph
4.96 out of 5 average rating, 386 reviews4 Season Lower Yurt Stay on VT Homestead
2–9 Apr
Chalet in Killington
4.9 out of 5 average rating, 159 reviewsClose to Mountain and walk to restaurants!
1–8 Jul
Home in Killington
4.89 out of 5 average rating, 273 reviewsKillington Mountain Retreat: Groups|Hot Tub|Games
14–21 Jun
Loft in Monroe
4.94 out of 5 average rating, 194 reviewsThe Loft at River's Edge w/hot tub!
26 Apr – 3 May
Flat in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
18–25 Oct
Chalet in Killington
5.0 out of 5 average rating, 117 reviewsLuxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard
15–22 Jul
Family- and pet-friendly home rentals
Home in Rochester
4.9 out of 5 average rating, 282 reviewsMountain Home ready for you!
17–24 Oct
Cottage in Lincoln
4.87 out of 5 average rating, 857 reviewsThe Barn at North Orchard, Near Middlebury
2–9 Sept
Guest house in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
22–29 Apr
Cottage in Brandon
4.91 out of 5 average rating, 266 reviewsHenrietta’s Hideaway-Walk Downtown!
7–14 Apr
Guest house in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
30 Aug – 6 Sept
Guest house in Granville
4.9 out of 5 average rating, 786 reviewsMoon Valley Country Retreat no clean fee pets yes
6–13 Dec
Guest house in Hartland
4.95 out of 5 average rating, 913 reviewsYurt In The Woods - Private Refuge
24 Feb – 3 Mar
Home in Goshen
4.82 out of 5 average rating, 251 reviewsNature Lover's Paradise
9–16 Aug
Family-friendly home rentals with a pool
Home in Granville
4.95 out of 5 average rating, 107 reviewsEpic Views of the Green Mountains
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
21–28 Aug
Apartment in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
17–24 Apr
Cabin in Bridport
4.92 out of 5 average rating, 133 reviewsChamplain Valley Alpacas
13–20 Oct
Flat in Barre
4.94 out of 5 average rating, 156 reviewsRelax in Recreation Paradise!
11–18 Sept
Guest suite in Ryegate
4.91 out of 5 average rating, 211 reviewsSecluded Paradise on the Connecticut River, VT
4–11 Jul
Guest house in Ticonderoga
4.99 out of 5 average rating, 197 reviewsChilson Brook Alpacas
12–19 Nov
Cabin in Haverhill
4.92 out of 5 average rating, 418 reviewsSecluded Lumberjack Cabin w/ Hot Tub, Pool & Lake
1–8 Feb
Quick stats about holiday 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
£88 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
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