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
Cottage in Shaftsbury
4.99 out of 5 average rating, 599 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Mar 26 – Apr 2
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 30 – Jun 6
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
Dec 17 – 24
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Mar 18 – 25
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
Jul 21 – 28
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec 22 – 29
Apartment in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
Nov 27 – Dec 4
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Sep 8 – 15
Family- and pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Apr 6 – 13
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Jul 11 – 18
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Feb 22 – Mar 1
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Aug 19 – 26
Guest suite in Montague
4.93 out of 5 average rating, 163 reviewsGreat Falls Private Suite
Dec 19 – 26
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
May 1 – 8
Cottage in Bernardston
4.88 out of 5 average rating, 286 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Mar 20 – 27
Apartment in Cambridge
4.91 out of 5 average rating, 370 reviewsWake up to spectacular views!
Apr 25 – May 2
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 10 – 17
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Nov 15 – 22
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
Sep 21 – 28
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Sep 23 – 30
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
May 5 – 12
Apartment in Rexford
4.96 out of 5 average rating, 324 reviewsNeed a Getaway??
Oct 31 – Nov 7
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct 31 – Nov 7
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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