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
6–13 Jun
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
20–27 Mar
Cabin in Saugerties
4.86 out of 5 average rating, 173 reviewsContainer Cabin in the Catskills (Field)
30 Sep – 7 Oct
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
26 Jan – 2 Feb
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
28 May – 4 Jun
Flat in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
4–11 Dec
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
24 Feb – 3 Mar
Home in Northampton
4.88 out of 5 average rating, 568 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
1–8 Jul
Family- and pet-friendly home rentals
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
31 Mar – 7 Apr
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
25 Apr – 2 May
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
4–11 Sep
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
1–8 Mar
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 583 reviewsMagic Forest Farm's Mountain View Suite
13–20 Sep
Tiny home in Jamaica
4.94 out of 5 average rating, 1146 reviewsApple Blossom Cottage: A Tiny House
4–11 Apr
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
17–24 Dec
Cottage in Bernardston
4.88 out of 5 average rating, 287 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
13–20 Mar
Family-friendly home rentals with a pool
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
31 Aug – 7 Sep
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
22–29 Aug
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
10–17 Nov
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
19–26 Jul
Flat in Rexford
4.96 out of 5 average rating, 327 reviewsNeed a Getaway??
15–22 Jan
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
8–15 Oct
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
17–24 Sep
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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- Philadelphia Holiday rentals
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