
Family-friendly vacation rentals in Western Massachusetts
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Western Massachusetts
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 Western Massachusetts family-friendly rentals
Family-friendly home rentals with a hot tub

Artist Cottage

Sweet suite, walk to town tout suite!

Relaxing secluded stay with loving social animals.

Beautiful Timber Frame Retreat

The Creation Station

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Hilltown Cabin Hideaway: A River Runs Through It!

Special Retreat in Nature, Woodfired Tub
Family- and pet-friendly home rentals

Trainmaster's Inn - Caboose

Rustic Cabin in foothills of Green Mountains

Off Grid Yurt Right By The Best of The Berkshires

400+ Airbnb Visits: Incredible Mountain Cabin

Peaceful Cabin in the Woods

Berkshires Cottage by Lake. Year Round Adventures.

Runamuk Farm

Mill River Cottage (pet friendly!)
Family-friendly home rentals with a pool

Cozy private apt 8 mins from UCONN - solar powered

Affordable In-Law Apartment in Brooklyn, CT

Moon Valley Country Retreat no clean fee pets yes

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Peaceful apartment on 3.5 acres w/ Artist studio.

Silver Brook Cabin

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Hollywood Bungalow in the Berkshires #C0191633410
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Jersey Shore Vacation rentals
- Mount Pocono Vacation rentals
- South Jersey Vacation rentals
- The Hamptons Vacation rentals
- Luxury rentals Western Massachusetts
- House rentals Western Massachusetts
- Cottage rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a home theater Western Massachusetts
- Rentals with a hot tub Western Massachusetts
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- Rentals with a patio Western Massachusetts
- Apartment rentals Western Massachusetts
- Chalet rentals Western Massachusetts
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- Bed and breakfasts Western Massachusetts
- Condo rentals Western Massachusetts
- Rentals with pools Western Massachusetts
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- Ski-in/ski-out rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Rentals with a sauna Western Massachusetts
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- Private suite rentals Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Tiny house rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Rentals with beach access Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Hotel rentals Western Massachusetts
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- Fitness-friendly rentals Western Massachusetts
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Brimfield State Forest
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Bigelow Hollow State Park
- Taconic State Park
- Dinosaur State Park
- Mount Sugarloaf State Reservation
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Hartford Golf Club
- Beartown State Forest
- Mount Snow Ski Resort
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Albany Center Gallery
- Bousquet Mountain Ski Area