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
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Cottage in Shaftsbury
4.99 out of 5 average rating, 605 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Cabin in Saugerties
4.86 out of 5 average rating, 175 reviewsContainer Cabin in the Catskills (Field)
Bungalow in Easthampton
4.92 out of 5 average rating, 436 reviewsThe Creation Station
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Home in Round Top
4.96 out of 5 average rating, 162 reviewsEscape in the Catskills w/hottub
Home in Northampton
4.88 out of 5 average rating, 569 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Family- and pet-friendly home rentals
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 584 reviewsMagic Forest Farm's Mountain View Suite
Cottage in Craryville
4.91 out of 5 average rating, 483 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Cottage in Lanesborough
4.85 out of 5 average rating, 252 reviewsWildlife Lakeside Cottage
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Cottage in Bernardston
4.88 out of 5 average rating, 289 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Cabin in Red Hook
4.96 out of 5 average rating, 308 reviewsModern Upstate Cabin, near Rhinebeck NY
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Apartment in Rexford
4.96 out of 5 average rating, 328 reviewsNeed a Getaway??
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Apartment in Northampton
4.97 out of 5 average rating, 247 reviewsSunny Inspirit Apartment in best downtown location
Quick stats about vacation rentals that are family-friendly in Pittsfield
Total rentals
120 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
40 properties allow pets
Total number of reviews
4.2K reviews
Nightly prices starting at
$10 before taxes and fees
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