
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

Luxury Fox Hollow Home-Laurel Lake

Updated Berkshires Chalet Mins to Tanglewood/Lenox

Beautiful House By The Lake W/Jetted Hot Tub

Spectacular Berkshire Retreat on Private Lake

Vacation Village in the Berkshires Resort Suite A

Vacation Village in the Berkshires Resort Suite B

My Mountain Haven- The Perfect Escape

Riverfront Getaway
Family- and pet-friendly home rentals

Charming Home in Lee

Elmwood Farmhouse

The Hideaway: Berkshire Home - village of Egremont

Berkshires hideaway! Hikes & serenity near lake

Secluded but not isolated Berkshire Retreat

Beautifully Nestled Berkshires Home

Brooksong, the perfect Berkshires getaway

Relaxing Housatonic Retreat
Family-friendly home rentals with a pool

Dream Vacation

Jiminy Peak Peaceful Home in Berkshires

Berkshire Lakefront Home W/Pool-100%Renovated

Fun Farmhouse

Berkshire Lake House, gunite pool, Chef's Kitchen

Wyndham Bentley Brook ** 2BR Deluxe

Beautiful 2BD Villa in Berkshires Resort

Cozy Condo @ Jiminy Peak
Destinations to explore
- Guesthouse rentals Berkshire County
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- Farmstay rentals Berkshire County
- Rentals with pools Berkshire County
- Pet-friendly rentals Berkshire County
- Private suite rentals Berkshire County
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- Rentals with a washer and dryer Berkshire County
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- Rentals with a hot tub Berkshire County
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- Rentals with lake access Berkshire County
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- Jiminy Peak Mountain Resort
- Six Flags New England
- John Boyd Thacher State Park
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Bash Bish Falls State Park
- Bushnell Park
- Taconic State Park
- Mount Snow Ski Resort
- Berkshire East Mountain Resort
- Zoom Flume
- Mount Greylock Ski Club
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Norman Rockwell Museum
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Keney Park Golf Course
- Pineridge Cross Country Ski Area
- Bull's Bridge Golf Club