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
Home
4.89 out of 5 average rating, 282 reviews25 Rocky Ridge Road: Ski Home for Groups. Lift Tix
Home
4.95 out of 5 average rating, 236 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Chalet
4.83 out of 5 average rating, 235 reviewsKillington Chalet - Hot Tub, Sauna, Boot Dryer
Condo
4.78 out of 5 average rating, 287 reviewsSerene Top Floor Condo (resort style amenities)
Chalet
4.87 out of 5 average rating, 241 reviewsLarge Chalet; Sauna, Hot Tub; Walk to Trail
Condo
4.96 out of 5 average rating, 126 reviews#45 Luxury Ski & Summer Condo with Private Sauna
Condo
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Home
4.96 out of 5 average rating, 202 reviewsBrthtkng New Premier Lake Champlain Wfrnt Escape!
Family- and pet-friendly home rentals
Cabin
4.97 out of 5 average rating, 143 reviewsThe Cozy Little Red Cabin
Cabin
4.95 out of 5 average rating, 198 reviewsHideaway Cabin by the Stream on 27 Acres
Cabin
5 out of 5 average rating, 259 reviewsPine Cabin, Galusha Hill Farm, incredible view!
Guesthouse
4.97 out of 5 average rating, 258 reviewsGroton Forest Retreat
Rental unit
4.98 out of 5 average rating, 408 reviewsPrivate Hilltop farm apartment
Home
4.96 out of 5 average rating, 214 reviewsComfortable farmhouse with stunning views
Rental unit
4.87 out of 5 average rating, 662 reviewsEntire 2nd Floor Walk to Montpelier
Home
4.99 out of 5 average rating, 294 reviewsDawnside - Green Mtns Home with White Mtns View
Family-friendly home rentals with a pool
Guesthouse
5 out of 5 average rating, 210 reviewsChilson Brook Alpacas
Rental unit
4.94 out of 5 average rating, 161 reviewsRelax in Recreation Paradise!
Condo
4.93 out of 5 average rating, 88 reviewsCozy 1-bed, Mountain Green Resort - Killington, VT
Condo
4.74 out of 5 average rating, 65 reviewsKillington Vermont Luxury 2 bed condo
Condo
4.95 out of 5 average rating, 98 reviews⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
Condo
4.97 out of 5 average rating, 119 reviewsTWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
Home
4.91 out of 5 average rating, 87 reviewsComfortable, relaxing large country home
Townhouse
4.97 out of 5 average rating, 64 reviewsSpacious Quiet Family Condo in Killington, VT
Quick stats about vacation rentals that are family-friendly in Pittsfield
Total rentals
50 properties
Nightly prices starting at
€ 129 before taxes and fees
Total number of reviews
2.3K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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