Family-friendly vacation rentals in Berkshire County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Berkshire 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 Berkshire County family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 5 – 12
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Feb 20 – 27
Home in Hancock
4.85 out of 5 average rating, 41 reviewsJiminy Peak Peaceful Home in Berkshires
Mar 10 – 17
Home in East Chatham
4.78 out of 5 average rating, 172 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Aug 14 – 21
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
Sep 1 – 8
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot tub Tennis Court&Pool
May 6 – 13
Apartment in Lee
4.82 out of 5 average rating, 45 reviewsLee time-share near ski hiking music
Jun 19 – 24
Family- and pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Mar 23 – 30
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
Jan 6 – 13
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
Apr 20 – 27
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
Sep 24 – Oct 1
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Feb 27 – Mar 6
Home in Williamstown
4.81 out of 5 average rating, 171 reviewsWalking distance to downtown
Aug 28 – Sep 4
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
May 13 – 20
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Sep 4 – 11
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 29 – Sep 5
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Jan 10 – 17
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Sep 28 – Oct 5
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Nov 21 – 28
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Apr 26 – May 3
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews*February/March Special*"Too Good" AKA 2 Goodrich
Nov 21 – 28
Home in Sandisfield
4.96 out of 5 average rating, 24 reviewsPrivate gem in the Berkshires on the Buck River
May 23 – 30
Home in Stephentown
4.9 out of 5 average rating, 10 reviewsBerkshire Beauty
Jan 29 – Feb 5
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