Family-friendly holiday 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.
Holiday rentals for every style
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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, 251 reviewsAmazing Berkshire Mountains Cabin
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @Jiminy Peak
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Home in Hancock
4.85 out of 5 average rating, 41 reviewsJiminy Peak Peaceful Home in Berkshires
Home in East Chatham
4.78 out of 5 average rating, 172 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot Tub, Tennis Court & Pool
Apartment in Lee
4.82 out of 5 average rating, 45 reviewsLee time-share near ski hiking music
Family- and pet-friendly home rentals
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
Home in Williamstown
4.81 out of 5 average rating, 171 reviewsWalking distance to downtown
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews*February/March Special*"Too Good" AKA 2 Goodrich
Home in Stephentown
4.9 out of 5 average rating, 10 reviewsBerkshire Beauty
Home in Sandisfield
4.96 out of 5 average rating, 24 reviewsPrivate gem in the Berkshires on the Buck River
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