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

Updated Berkshires Chalet Mins to Tanglewood/Lenox

Spectacular Berkshire Retreat on Private Lake

The Inn at Quail Run- Guest House

Secluded Farmhouse Retreat - stunning views

Jiminy Peak Peaceful Home in Berkshires

Large Family Home Near Five Colleges

The Farmhouse - Hot tub eclectic farmhouse 3 br

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Family- and pet-friendly home rentals

Dog Friendly Studio

Farm Fresh Feeding Hills

The Carriage Barn

Light-filled Studio Apt. Near Smith

Stone n' Sky Lodge

19th c. Barn in The Berkshires
Flamig Farm Staycation

Secluded Berkshire cabin with scenic views
Family-friendly home rentals with a pool

Cozy private apt 8 mins from UCONN - solar powered

Rustic Sunny Vermont Home near Mount Snow

The Creation Station

Berkshire Lakefront Home W/Pool-100%Renovated

Sweet cape near U Mass

Luxury Home * Pool * Fireplace

Light-bathed 3br w porch in best downtown location

Hollywood Bungalow in the Berkshires #C0191633410
Destinations to explore
- Hudson Valley Vacation rentals
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- Rentals with a patio Pioneer Valley
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- Rentals with a fire pit Pioneer Valley
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- Pet-friendly rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
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- Family-friendly rentals Massachusetts
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- Six Flags New England
- Monadnock State Park
- TPC River Highlands
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Brownstone Adventure Sports Park
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Dinosaur State Park
- The Shattuck Golf Club
- Mohawk Mountain Ski Area
- Beartown State Forest
- Talcott Mountain State Park
- Wintonbury Hills Golf Course
- Douglas State Forest
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area