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
Home in East Chatham
4.79 out of 5 average rating, 184 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Home in Craryville
4.98 out of 5 average rating, 205 reviewsModern Home in Woods w/ Hot Tub 10 Miles to Hudson
Home in Rhinebeck
4.91 out of 5 average rating, 224 reviewsRhinebeck Modern Home with amazing outdoor space
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Home in Chester
4.96 out of 5 average rating, 337 reviewsRiverfront Getaway
Condo in Hancock
4.85 out of 5 average rating, 142 reviewsCozy Condo @ Jiminy Peak
Home in Wilmington
4.83 out of 5 average rating, 162 reviewsThe Vermont Barn (Mount Snow)
Home in Wilmington
4.91 out of 5 average rating, 139 reviewsMartin Ski Barn - 4BR Ski House, 15 min to Mt Snow
Family- and pet-friendly home rentals
Cottage in Craryville
4.91 out of 5 average rating, 517 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Farm stay in Ghent
4.91 out of 5 average rating, 229 reviewsRetrograss Farm Apartment
Home in Saugerties
4.97 out of 5 average rating, 123 reviewsWelcome to Malden Manor, in a prime location!
Home in Ghent
4.9 out of 5 average rating, 274 reviewsRenovated guesthouse on 52 acres!
Home in Ancram
4.82 out of 5 average rating, 109 reviewsSecluded Post-And-Beam Retreat
Cottage in Greenville
4.92 out of 5 average rating, 211 reviewsHistoric farmhouse escape on 14 scenic acres
Vacation home in Hudson
4.9 out of 5 average rating, 106 reviews2 blocks to Warren ST w/ a yard and parking
Cottage in Lanesborough
4.84 out of 5 average rating, 274 reviewsWildlife Lakeside Cottage
Family-friendly home rentals with a pool
Chalet in Catskill
4.96 out of 5 average rating, 184 reviewsDaydream Mountain Art-Chateau '73 | I ❤️ Catskill
Townhouse in Dover
4.96 out of 5 average rating, 143 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Home in Germantown
4.98 out of 5 average rating, 48 reviewsColumbia County Farmhouse with Pool
Home in Ghent
4.88 out of 5 average rating, 302 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Saugerties
4.94 out of 5 average rating, 139 reviewsUpstate Family Farmhouse 5BR Woodstove Fenced Yard
Rental unit in Rexford
4.96 out of 5 average rating, 358 reviewsNeed a Getaway??
Home in Canaan
4.99 out of 5 average rating, 83 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Cabin in Red Hook
4.96 out of 5 average rating, 337 reviewsModern Upstate Cabin, near Rhinebeck NY
Quick stats about vacation rentals that are family-friendly in Pittsfield
Total rentals
110 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
4.8K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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