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 in Plymouth
4.95 out of 5 average rating, 237 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Chalet in Killington
4.83 out of 5 average rating, 235 reviewsKillington Chalet - Hot Tub, Sauna, Boot Dryer
Rental unit in Hinesburg
4.91 out of 5 average rating, 253 reviewsBackyard Bunker Retreat
Yurt in Randolph
4.95 out of 5 average rating, 416 reviews4 Season Lower Yurt Stay on VT Homestead
Cabin in Londonderry
4.82 out of 5 average rating, 446 reviewsStunning Rustic Apple Barn - hot tub & sauna
Condo in Killington
4.96 out of 5 average rating, 128 reviews#45 Luxury Ski & Summer Condo with Private Sauna
Rental unit in Londonderry
4.96 out of 5 average rating, 568 reviewsVermont Getaway Apartment
Home in Addison
4.96 out of 5 average rating, 202 reviewsBrthtkng New Premier Lake Champlain Wfrnt Escape!
Family- and pet-friendly home rentals
Cabin in West Windsor
4.97 out of 5 average rating, 132 reviewsCowshed Cabin Farm
Cabin in Cavendish
4.96 out of 5 average rating, 145 reviewsThe Cozy Little Red Cabin
Guesthouse in Groton
4.97 out of 5 average rating, 258 reviewsGroton Forest Retreat
Cabin in Topsham
4.99 out of 5 average rating, 263 reviewsPine Cabin, Galusha Hill Farm, incredible view!
Rental unit in Andover
4.98 out of 5 average rating, 409 reviewsPrivate Hilltop farm apartment
Home in Danby
4.96 out of 5 average rating, 215 reviewsComfortable farmhouse with stunning views
Guesthouse in Hartland
4.95 out of 5 average rating, 960 reviewsYurt In The Woods - Private Refuge
Cabin in Elizabethtown
4.87 out of 5 average rating, 816 reviewsBell Crest Cabin, 1 bedroom
Family-friendly home rentals with a pool
Home in Salem
4.98 out of 5 average rating, 185 reviewsMagical Farm Getaway - a must visit!
Guesthouse in Ticonderoga
5 out of 5 average rating, 210 reviewsChilson Brook Alpacas
Guest suite in Ryegate
4.92 out of 5 average rating, 226 reviewsSecluded Paradise on the Connecticut River, VT
Rental unit in Barre
4.94 out of 5 average rating, 162 reviewsRelax in Recreation Paradise!
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
Condo in Warren
4.97 out of 5 average rating, 119 reviewsTWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
Condo in Killington
4.82 out of 5 average rating, 251 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Quick stats about vacation rentals that are family-friendly in Pittsfield
Total rentals
50 properties
Nightly prices starting at
$140 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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