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
Apr 7 – 14
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, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Apr 5 – 12
Home in Hancock
4.85 out of 5 average rating, 41 reviewsJiminy Peak Peaceful Home in Berkshires
Mar 11 – 18
Home in East Chatham
4.78 out of 5 average rating, 172 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Sep 16 – 23
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
Sep 21 – 28
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot tub Tennis Court&Pool
Oct 20 – 27
Apartment in Lee
4.82 out of 5 average rating, 45 reviewsLee time-share near ski hiking music
Jul 28 – Aug 2
Family- and pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Feb 4 – 11
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
Nov 7 – 14
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Feb 26 – Mar 5
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
Sep 24 – Oct 1
Home in Williamstown
4.81 out of 5 average rating, 171 reviewsWalking distance to downtown
Feb 1 – 8
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
May 12 – 19
Cabin in Monterey
4.93 out of 5 average rating, 186 reviewsExotic Mountain Retreat in the Berkshires
May 31 – Jun 7
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 28 – Sep 4
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Apr 14 – 21
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Sep 27 – Oct 4
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Dec 3 – 10
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Nov 22 – 29
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews*February/March Special*"Too Good" AKA 2 Goodrich
Nov 20 – 27
Home in Sandisfield
4.96 out of 5 average rating, 24 reviewsPrivate gem in the Berkshires on the Buck River
May 22 – 29
Home in Stephentown
4.9 out of 5 average rating, 10 reviewsBerkshire Beauty
Dec 8 – 15
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