
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

The Bear's Den

Berkshire Mountain Top Chalet

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

Cozy Guesthouse Near Downtown, Lee

3-bedroom Berkshire bungalow on 2.5 peaceful acres

The East Street Cabin

Off Grid Yurt Right By The Best of The Berkshires

Quaint Suite in Center of Adams

King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi

Swiss Chalet Style Timberframe Home in Berkshires

Cottage on Scenic Road
Family-friendly home rentals with a pool

Quiet Studio in Desirable Neighborhood

The Catamount Ski Haus with Pool & Hot Tub

Stunning luxury home with pool

Enjoy every season the Berkshires have to offer.

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

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

Stylish Rural Sanctuary! (+ Summer Pool)

Hollywood Bungalow in the Berkshires #C0191633410
Destinations to explore
- Rentals with lake access Berkshire County
- House rentals Berkshire County
- Waterfront rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Beachfront rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Private suite rentals Berkshire County
- Rentals with beach access Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with breakfast Berkshire County
- Aparthotel rentals Berkshire County
- Farmstay rentals Berkshire County
- Rentals with a patio Berkshire County
- Cottage rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Bed and breakfasts Berkshire County
- Guesthouse rentals Berkshire County
- Chalet rentals Berkshire County
- Rentals with pools Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with an EV charger Berkshire County
- Rentals with a washer and dryer Berkshire County
- Fitness-friendly rentals Berkshire County
- Apartment rentals Berkshire County
- Hotel rentals Berkshire County
- Rentals with a fire pit Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with a sauna 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
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Hartford Golf Club
- Beartown State Forest
- Mount Snow Ski Resort
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area