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
May 28 – Jun. 4
Cottage in Shaftsbury
4.99 out of 5 average rating, 598 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Feb. 6 – 13
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Nov. 9 – 16
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
Jun. 10 – 15
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec. 25 – Jan. 1
Home in Round Top
4.96 out of 5 average rating, 160 reviewsEscape in the Catskills w/hottub
May 16 – 23
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Sep. 8 – 15
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Mar. 22 – 29
Family- and pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 250 reviewsWildlife Lakeside Cottage
Feb. 22 – Mar. 1
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Oct. 14 – 21
Cottage in Craryville
4.91 out of 5 average rating, 481 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Apr. 7 – 14
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Dec. 16 – 23
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Jul. 4 – 11
Cottage in Bernardston
4.88 out of 5 average rating, 286 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Dec. 30 – Jan. 6
Guest suite in Montague
4.93 out of 5 average rating, 163 reviewsGreat Falls Private Suite
Dec. 14 – 21
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
May 1 – 8
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Nov. 12 – 19
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep. 7 – 14
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
May 3 – 10
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Apr. 7 – 14
Apartment in Rexford
4.96 out of 5 average rating, 324 reviewsNeed a Getaway??
Oct. 21 – 28
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Aug. 3 – 10
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
Jul. 17 – 24
Townhouse in Hudson
4.94 out of 5 average rating, 193 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
Oct. 6 – 13
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
$14 CAD before taxes and fees
Destinations to explore
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