Kid-friendly holiday rentals in Stockbridge
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Stockbridge
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in Lee
4.9 out of 5 average rating, 208 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Monterey
4.93 out of 5 average rating, 310 reviewsCharming cottage w/ gorgeous views.
Home in Canaan
5.0 out of 5 average rating, 137 reviewsCountry Cottage
Home in Great Barrington
4.96 out of 5 average rating, 216 reviewsJaw dropping mountain & lake views
Home in Chatham
4.9 out of 5 average rating, 149 reviews2BR Chatham Vlg. Park@Door Keyless 100% Smoke Free
Home in Lenox
4.93 out of 5 average rating, 211 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Home in Stockbridge
4.95 out of 5 average rating, 103 reviewsSun-filled, Charming Stockbridge Classic- In Town!
Home in Dalton
4.88 out of 5 average rating, 115 reviewsThe Yellow House
Family-friendly apartment rentals
Flat in Sheffield
5.0 out of 5 average rating, 323 reviewsHideaway with Spectacular Berkshire Views
Flat in Plainfield
4.97 out of 5 average rating, 239 reviewsSunny, light filled loft in 1873 Colonial
Flat in Petersburg
4.86 out of 5 average rating, 152 reviewsThe Beer Diviner Brewery Apartment
Flat in Lenox Dale
4.93 out of 5 average rating, 116 reviewsCharming 2BD apartment.
Flat in Plainfield
4.95 out of 5 average rating, 241 reviewsSunny carriage house apartment
Flat in Hudson
4.95 out of 5 average rating, 101 reviewsRestored 19th century farm house apartment
Flat in Great Barrington
4.94 out of 5 average rating, 132 reviewsGB Eclectic Victorian
Flat in Sheffield
4.92 out of 5 average rating, 124 reviewsPrivate Berkshire Barn Apartment
Family-friendly apartment rentals
Apartment in Windham
4.89 out of 5 average rating, 136 reviewsCozy Mountain hideaway Windham, Hunter
Apartment in Hudson
4.94 out of 5 average rating, 148 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Apartment in Hunter
4.97 out of 5 average rating, 430 reviews*Great Reviews* Hunter Mtn. Cozy/Clean/Close Condo
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Apartment in Lanesville
4.97 out of 5 average rating, 552 reviewsStylish Condo Ski on/ Ski off Hunter Mountain
Apartment in Poughkeepsie
4.97 out of 5 average rating, 227 reviewsSpacious and stylish entire one bedroom apartment.
Apartment in Brattleboro
4.92 out of 5 average rating, 288 reviewsPrivate & Quiet Studio Apt. in Vermont
Apartment in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Quick stats about holiday rentals that are kid-friendly in Stockbridge
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
€ 110 before taxes and fees
Destinations to explore
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