Family-friendly holiday 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.
Holiday 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
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Cabin in Saugerties
4.86 out of 5 average rating, 178 reviewsContainer Cabin in the Catskills (Field)
Home in Pittsfield
4.82 out of 5 average rating, 167 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 Hudson
4.95 out of 5 average rating, 251 reviewsLivingston Farmhouse Escape with hot tub and sauna
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in Shaftsbury
4.94 out of 5 average rating, 125 reviewsConverted Vermont Barn on 6.5 acres with hot tub
Home in Craryville
4.98 out of 5 average rating, 191 reviewsModern Home in Woods w/ Hot Tub 10 Miles to Hudson
Family- and pet-friendly home rentals
Cottage in Craryville
4.91 out of 5 average rating, 485 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 585 reviewsMagic Forest Farm's Mountain View Suite
Guest suite in Montague
4.93 out of 5 average rating, 166 reviewsGreat Falls Private Suite
Cottage in Lanesborough
4.85 out of 5 average rating, 252 reviewsWildlife Lakeside Cottage
Home in Dalton
4.92 out of 5 average rating, 172 reviewsBrooksong, the perfect Berkshires getaway
Farm stay in West Simsbury
4.95 out of 5 average rating, 438 reviewsFlamig Farm Staycation
Flat in Sandisfield
4.92 out of 5 average rating, 229 reviewsSunny Berkshire Studio Apartment
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 272 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
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, 124 reviewsLovely cabin by the stream
Flat in Rexford
4.96 out of 5 average rating, 330 reviewsNeed a Getaway??
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Townhouse in Hudson
4.94 out of 5 average rating, 196 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
Bungalow in Easthampton
4.92 out of 5 average rating, 438 reviewsThe Creation Station
Quick stats about holiday 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
€ 9 before taxes and fees
Destinations to explore
- New City Holiday rentals
- New Haven Holiday rentals
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- Catskill Holiday rentals
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