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
Cabin in Monterey
4.95 out of 5 average rating, 252 reviewsAmazing Berkshire Mountains Cabin
Cabin in Becket
5.0 out of 5 average rating, 256 reviewsWaldtreff - quiet grand cabin
Home in Pittsfield
4.82 out of 5 average rating, 166 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Home in East Chatham
4.78 out of 5 average rating, 172 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Farm stay in Hillsdale
4.96 out of 5 average rating, 118 reviewsPixley Knob Hill Farm (1818)
Cottage in Becket
4.61 out of 5 average rating, 145 reviewsA Magical Spot on Little Robin Lake
Home in Lee
4.96 out of 5 average rating, 75 reviewsSpectacular Berkshire Retreat on Private Lake
Chalet in Richmond
4.98 out of 5 average rating, 86 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
Family- and pet-friendly home rentals
Home in Williamstown
4.81 out of 5 average rating, 173 reviewsWalking distance to downtown
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Cottage in Lanesborough
4.85 out of 5 average rating, 252 reviewsWildlife Lakeside Cottage
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Home in Dalton
4.92 out of 5 average rating, 172 reviewsBrooksong, the perfect Berkshires getaway
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
Home in Cheshire
4.85 out of 5 average rating, 200 reviews19th c. Barn in The Berkshires
Family-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
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
4.98 out of 5 average rating, 40 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews*Special May Pricing* "Too Good" AKA 2 Goodrich
Home in Hancock
4.85 out of 5 average rating, 41 reviewsJiminy Peak Peaceful Home in Berkshires
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot Tub, Tennis Court & Pool
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