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
Get the amount of space that is right for you
Popular amenities for Berkshire County family-friendly rentals
Family-friendly home rentals with a hot tub
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
Jun 5 – 12
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec 20 – 27
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun 4
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Nov 9 – 16
Home in Hancock
4.85 out of 5 average rating, 41 reviewsJiminy Peak Peaceful Home in Berkshires
Dec 30 – Jan 6
Home in East Chatham
4.78 out of 5 average rating, 172 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Aug 17 – 24
Cottage in Becket
4.6 out of 5 average rating, 143 reviewsA Magical Spot on Little Robin Lake
Jun 5 – 12
Home in Canaan
4.71 out of 5 average rating, 55 reviewsPrivate estate with Hot tub Tennis Court&Pool
Sep 15 – 22
Family- and pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 250 reviewsWildlife Lakeside Cottage
Feb 14 – 21
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Oct 23 – 30
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
Nov 19 – 26
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
Nov 12 – 19
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Nov 4 – 11
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
Sep 9 – 16
Home in Williamstown
4.81 out of 5 average rating, 170 reviewsWalking distance to downtown
May 22 – 29
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
May 6 – 13
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 8 – 15
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Dec 4 – 11
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jul 8 – 15
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Jan 25 – Feb 1
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Dec 9 – 16
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews*February/March Special*"Too Good" AKA 2 Goodrich
Feb 11 – 18
Home in Sandisfield
4.96 out of 5 average rating, 24 reviewsPrivate gem in the Berkshires on the Buck River
May 15 – 22
Home in Canaan
4.99 out of 5 average rating, 68 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Apr 23 – 30
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