
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

Berkshire Mountain Top Chalet

The Catamount Ski Haus with Pool & Hot Tub

Art House! Spacious Getaway By Mass Moca

Cabin in the woods w cedar Hot Tub + private pond

Luxury Cabin | Fall Foliage, & Autumn Adventures

Elegant Year-Round Lakeside Retreat with AC

Hot Tub, Canoe, Hike, Dog Friendly, Berkshires!

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
Family- and pet-friendly home rentals

3-bedroom Berkshire bungalow on 2.5 peaceful acres

The East Street Cabin

Carriage house with Chef's Kitchen, close to town

Off Grid Yurt Right By The Best of The Berkshires

Private Berkshire Barn Apartment

Quaint Suite in Center of Adams

Swiss Chalet Style Timberframe Home in Berkshires

Enjoy every season the Berkshires have to offer.
Family-friendly home rentals with a pool

Quiet Studio in Desirable Neighborhood

The Nest at Birdland

Stunning luxury home with pool

Red Rock Summit: Mtn Escape w/ Pool, Pond + Views

Jiminy Peak Country Inn - ski in/out condo MT view

Hilltop: Panoramic Views w/ Pool near Catamount

Stylish Rural Sanctuary! (+ Summer Pool)

Hollywood Bungalow in the Berkshires #C0191633410
Destinations to explore
- Beachfront rentals Berkshire County
- Guest house rentals Berkshire County
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- Aparthotel rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Cottage rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Rentals with breakfast Berkshire County
- Rentals with beach access Berkshire County
- Waterfront rentals Berkshire County
- House rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Rentals with a patio Berkshire County
- Hotel rentals Berkshire County
- Farm stay rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Chalet rentals Berkshire County
- Flat rentals Berkshire County
- Bed and breakfasts Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with lake access Berkshire County
- Rentals with pools Berkshire County
- Private suite rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Bushnell Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Wintonbury Hills Golf Course
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Taconic State Park
- Mount Sugarloaf State Reservation
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Beartown State Forest
- Bousquet Mountain Ski Area
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Albany Center Gallery
- Hancock Shaker Village
- Mount Snow Ski Resort
- Northern Cross Vineyard