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

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

Rhinebeck Home with an amazing outdoor space+H/tub

Country Getaway Lodge / Ranch

Mt Snow Ski In/Out at Seasons

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Peaceful Hudson Valley Retreat House with HOT TUB!

Peaceful cabin close to skiing & Brattleboro

Time to Relax, close to Saratoga.
Family- and pet-friendly home rentals

Mountaintop Skyloft

Cedar Wet Room w Soaking Tub

Welcome to Malden Manor, in a prime location!

Berkshires hideaway! Hikes & serenity near lake
Flamig Farm Staycation

Historic farmhouse escape on 14 scenic acres

2 blocks to Warren ST w/ a yard and parking

Magic Forest Farm’s Purple Palace
Family-friendly home rentals with a pool

Daydream Mountain Art-Chateau | Hot Tub & Pool

Bear's Den - Mt Snow Townhome w/ Heated Pool!

Spacious Staycation near HITS & the Hudson

Modern Barn on 12 acres w Sauna, FirePit+swimming

5BR close to Village | Diamond Mills | HITS | Pool

Need a Getaway??

Modern Upstate Cabin, near Rhinebeck NY

1880s sun-bathed beauty in best downtown location
Quick stats about vacation rentals that are family-friendly in Pittsfield
Total rentals
120 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
5K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Stratton Mountain
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- Six Flags New England
- Catamount Mountain Ski Resort
- Albany Center Gallery
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Mount Snow Ski Resort
- Berkshire East Mountain Resort
- Taconic State Park
- Zoom Flume
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Bright Nights at Forest Park
- Hancock Shaker Village
- Kent Falls State Park
- Beartown State Forest
- Pineridge Cross Country Ski Area
- Naumkeag
- Otis Ridge
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