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
Condo in Hancock
Cozy Condo @ Jiminy Peak
Cabin in Monterey
Amazing Berkshire Mountains Cabin
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
Home in Hancock
Jiminy Peak Peaceful Home in Berkshires
Home in East Chatham
Hot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Farm stay in Hillsdale
Pixley Knob Hill Farm (1818)
Home in Canaan
Private estate with Hot Tub, Tennis Court & Pool
Cottage in Becket
A Magical Spot on Little Robin Lake
Family- and pet-friendly home rentals
Farm stay in New Ashford
Sheep Barn on the Greylock Valley Estate
Home in Dalton
Brooksong, the perfect Berkshires getaway
Cottage in Lanesborough
Wildlife Lakeside Cottage
Cabin in Lee
Spring sale! Cabin with views in the Berkshires
Rental unit in Great Barrington
Secluded but not isolated Berkshire Retreat
Home in Cheshire
19th c. Barn in The Berkshires
Home in Great Barrington
Your own private Berkshires retreat
Home in Williamstown
Walking distance to downtown
Family-friendly home rentals with a pool
Bungalow in Williamstown
Hollywood Bungalow in the Berkshires
Home in Sheffield
Race Mountain House
Home in Great Barrington
Berkshire Country Estate! Pool & Tennis Court -GB
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
Home in Stockbridge
.1 miles from down town Stockbridge on 11 acres!
Home in Sandisfield
Private gem in the Berkshires on the Buck River
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Home in Stephentown
Berkshire Beauty
Destinations to explore
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- Family-friendly rentals Massachusetts
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