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
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @Jiminy Peak
19–26 Mar
Cottage in Shaftsbury
4.99 out of 5 average rating, 599 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
23–30 Jan
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
26 Mar – 2 Apr
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
18–25 Oct
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
21–28 Jul
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
24–31 Dec
Apartment in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
17–24 Oct
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
22–29 Jun
Family- and pet-friendly home rentals
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
31 Mar – 7 Apr
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
6–13 Feb
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
24 Feb – 3 Mar
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
16–23 Mar
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
2–7 May
Guest suite in Montague
4.93 out of 5 average rating, 163 reviewsGreat Falls Private Suite
22–29 Sep
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
28 Jul – 4 Aug
Chalet in Dover
4.93 out of 5 average rating, 265 reviewsA charming VT chalet
14–21 Oct
Family-friendly home rentals with a pool
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
25 Sep – 2 Oct
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
23–30 Jan
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
5–12 Dec
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
8–15 Oct
Apartment in Rexford
4.96 out of 5 average rating, 325 reviewsNeed a Getaway??
20–27 Apr
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
25 Sep – 2 Oct
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
11–18 Oct
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
$17 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
- New Haven Holiday rentals
- Lake George Holiday rentals
- Catskill Holiday rentals
- Albany Holiday rentals
- Catskill Mountains Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals New York
- Family-friendly rentals New Hampshire
- Family-friendly rentals Massachusetts
- Rentals with a fire pit Pittsfield
- Rentals with a fireplace Pittsfield
- Monthly Rentals Pittsfield
- Rentals with a washing machine and dryer Pittsfield
- Rentals with a patio Pittsfield
- Rentals with pools Pittsfield
- Waterfront rentals Pittsfield
- House rentals Pittsfield
- Rentals with outdoor seating Pittsfield
- Apartment rentals Pittsfield
- Pet-friendly rentals Pittsfield
- Rentals with lake access Pittsfield
- Kid-friendly rentals Pittsfield
- Family-friendly rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom