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
Apr 7 – 14
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Mar 6 – 13
Cabin in Saugerties
4.86 out of 5 average rating, 173 reviewsContainer Cabin in the Catskills (Field)
Mar 16 – 23
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Feb 21 – 28
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
Jul 23 – 30
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
Jun 11 – 18
Apartment in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
Oct 20 – 27
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 7 – 14
Family- and pet-friendly home rentals
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
Oct 13 – 20
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Mar 23 – 30
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Oct 30 – Nov 6
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Mar 10 – 17
Cottage in Bernardston
4.88 out of 5 average rating, 287 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Mar 24 – 31
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 582 reviewsMagic Forest Farm's Mountain View Suite
Oct 19 – 26
Apartment in Cambridge
4.91 out of 5 average rating, 370 reviewsMountain View Apartment! Close to Saratoga!
Apr 15 – 22
Apartment in Northampton
4.99 out of 5 average rating, 727 reviewsNorth Street Nest, sunny downtown apartment
Apr 8 – 15
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 29 – Sep 5
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Mar 22 – 29
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Jan 10 – 17
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 6 – 13
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct 21 – 28
Apartment in Rexford
4.96 out of 5 average rating, 327 reviewsNeed a Getaway??
Jan 26 – Feb 2
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
Oct 11 – 18
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
Destinations to explore
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