
Family-friendly holiday 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.
Holiday 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

Beautiful House By The Lake W/Jetted Hot Tub

Updated Berkshires Chalet Mins to Tanglewood/Lenox

Pixley Knob Hill Farm (1818)

Spectacular Berkshire Retreat on Private Lake

My Mountain Haven- The Perfect Escape

Riverfront Getaway

RANCH at FOX HOLLOW on Laurel Lake
Family- and pet-friendly home rentals

Charming Home in Lee

The East Street Cabin

The Hideaway: Berkshire Home - village of Egremont

Elmwood Farmhouse

Berkshires hideaway! Hikes & serenity near lake

Secluded but not isolated Berkshire Retreat

Beautifully Nestled Berkshires Home

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

Wyndham Bentley Brook ** 2BR Deluxe

Beautiful 2BD Villa in Berkshires Resort

Wyndham Bentley Brook * Studio

R3Bliss - Estate with Hot Tub, Tennis Court & Pool
Destinations to explore
- Rentals with an EV charger Berkshire County
- Rentals with a fireplace Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Waterfront rentals Berkshire County
- Guest house rentals Berkshire County
- Rentals with lake access Berkshire County
- Bed and breakfasts Berkshire County
- Rentals with breakfast Berkshire County
- Cottage rentals Berkshire County
- Rentals with a firepit Berkshire County
- Private suite rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Flat rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with a patio Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with pools Berkshire County
- Family-friendly rentals Berkshire County
- Farm stay rentals Berkshire County
- Hotel rentals Berkshire County
- House rentals Berkshire County
- Rentals with beach access Berkshire County
- Chalet rentals Berkshire County
- Rentals with a sauna Berkshire County
- Beachfront rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Family-friendly rentals Massachusetts
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- Pet-Friendly Vacation Rentals United States
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Bushnell Park
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Albany Center Gallery
- Beartown State Forest
- Talcott Mountain State Park
- Hartford Golf Club
- Wintonbury Hills Golf Course
- Opus 40
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Hancock Shaker Village