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
Home in Pittsfield
4.82 out of 5 average rating, 167 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!
Farm stay in Hillsdale
4.96 out of 5 average rating, 118 reviewsPixley Knob Hill Farm (1818)
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot Tub, Tennis Court & Pool
Cottage in Becket
4.61 out of 5 average rating, 145 reviewsA Magical Spot on Little Robin Lake
Rental unit in Lee
4.82 out of 5 average rating, 45 reviewsLee time-share near ski hiking music
Family- and pet-friendly home rentals
Rental unit in Sandisfield
4.92 out of 5 average rating, 229 reviewsSunny Berkshire Studio Apartment
Rental unit in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Home in Dalton
4.92 out of 5 average rating, 172 reviewsBrooksong, the perfect Berkshires getaway
Farm stay in New Ashford
4.9 out of 5 average rating, 224 reviewsSheep Barn on the Greylock Valley Estate
Cabin in Lee
4.9 out of 5 average rating, 103 reviewsSpring sale! Cabin with views in the Berkshires
Cottage in Lanesborough
4.85 out of 5 average rating, 254 reviewsWildlife Lakeside Cottage
Home in Cheshire
4.85 out of 5 average rating, 201 reviews19th c. Barn in The Berkshires
Cottage in Canaan
4.9 out of 5 average rating, 127 reviewsPlan your Berkshires by the lake
Family-friendly home rentals with a pool
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, 35 reviewsBerkshire Country Estate! Pool & Tennis Court -GB
Home in Pittsfield
4.98 out of 5 average rating, 41 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews.1 miles from down town Stockbridge on 11 acres!
Home in Sandisfield
4.96 out of 5 average rating, 24 reviewsPrivate gem in the Berkshires on the Buck River
Home in Canaan
4.99 out of 5 average rating, 73 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Home in Stephentown
4.9 out of 5 average rating, 10 reviewsBerkshire Beauty
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