Kid-friendly holiday rentals in The Berkshires
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in The Berkshires
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires family-friendly rentals
Kid-friendly house rentals
Home
4.84 out of 5 average rating, 170 reviewsA Victorian "Lady"
Home
4.96 out of 5 average rating, 148 reviewsSkiing and Breweries! Mountain and river views!
Home
5 out of 5 average rating, 46 reviews14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Home
4.88 out of 5 average rating, 221 reviewsEntire lake house to yourself. Great for groups
Home
4.75 out of 5 average rating, 28 reviewsKid/Baby-Friendly 3BD + In-Law Studio w Large Yard
Home
5 out of 5 average rating, 116 reviewsCheerful, quiet 3 bedroom home
Home
4.98 out of 5 average rating, 43 reviewsFamily Friendly Gataway in Hudson Valley
Home
4.84 out of 5 average rating, 102 reviewsLovely vacation home free st and share parking
Family-friendly apartment rentals
Flat
4.8 out of 5 average rating, 113 reviewsNice 2nd floor apt
Flat
4.76 out of 5 average rating, 129 reviewsCute, Convenient with Big Backyard
Flat
4.82 out of 5 average rating, 173 reviewsApartment on Main Street
Flat
4.9 out of 5 average rating, 165 reviewsPrivate 1BR Apartment 1 Block from Warren St.
Flat
4.99 out of 5 average rating, 208 reviewsCharming Efficiency
Flat
4.85 out of 5 average rating, 523 reviewsParkside downtown cozy apartment
Flat
4.82 out of 5 average rating, 281 reviewsUnwind in a Bespoke Downtown Studio W Laundry
Flat
4.88 out of 5 average rating, 285 reviews3 bedroom near Wesleyan, downtown
Family-friendly apartment rentals
Apartment
4.89 out of 5 average rating, 166 reviewsCozy Mountain hideaway Windham, Hunter
Apartment
4.99 out of 5 average rating, 107 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Apartment
4.87 out of 5 average rating, 230 reviewsMt Snow Ski In/Out at Seasons
Apartment
4.82 out of 5 average rating, 119 reviewsNew Britain "Joy of Small Space" Condo
Apartment
4.93 out of 5 average rating, 149 reviewsUpdated Ski in/Ski out Stratton Condo!
Apartment
4.98 out of 5 average rating, 107 reviewsCozy, spacious mountain condo
Apartment
4.93 out of 5 average rating, 86 reviewsGreat 2 bedroom condo at Stratton Mountain
Apartment
5 out of 5 average rating, 14 reviewsCozy 2 Bedroom Condo, Fireplace , outdoor deck
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