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
Nov 13 – 20
Cottage in Shaftsbury
4.99 out of 5 average rating, 599 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Dec 31 – Jan 7
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Mar 23 – 30
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec 23 – 30
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 13 – 20
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Sep 16 – 23
Home in Red Hook
4.88 out of 5 average rating, 212 reviewsWooded Retreat w/ Hot Tub and Trout River
Nov 7 – 14
Home in Hudson
4.84 out of 5 average rating, 222 reviewsHudson Country Cottage, Fireplace, Pond, Hot Tub
Mar 11 – 18
Family- and pet-friendly home rentals
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Mar 8 – 15
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Apr 19 – 26
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Apr 14 – 21
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
Feb 23 – Mar 2
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Jul 27 – Aug 3
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
May 1 – 8
Chalet in Dover
4.93 out of 5 average rating, 265 reviewsA charming VT chalet
Sep 20 – 27
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
May 31 – Jun 7
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 26 – Oct 3
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Mar 18 – 25
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Sep 11 – 18
Apartment in Rexford
4.96 out of 5 average rating, 324 reviewsNeed a Getaway??
Oct 31 – Nov 7
Apartment in Earlton
4.93 out of 5 average rating, 279 reviewsSweet Farm Stay
Jan 11 – 18
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Nov 17 – 24
Home in Catskill
4.95 out of 5 average rating, 175 reviewsDaydream Mountain Art-Chateau '73 | I ❤️ Catskill
Jun 6 – 13
Home in Saugerties
4.92 out of 5 average rating, 119 reviewsRedbarn House | Pool | Fire Pit | HITS | 4 BR
Sep 15 – 22
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
€ 9 before taxes and fees
Destinations to explore
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