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 Killington
4.89 out of 5 average rating, 282 reviews25 Rocky Ridge Road: Ski Home for Groups. Lift Tix
Home in Plymouth
4.95 out of 5 average rating, 236 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
Condo in Killington
4.78 out of 5 average rating, 287 reviewsSerene Top Floor Condo (resort style amenities)
Chalet in Killington
4.87 out of 5 average rating, 241 reviewsLarge Chalet; Sauna, Hot Tub; Walk to Trail
Condo in Killington
4.96 out of 5 average rating, 126 reviews#45 Luxury Ski & Summer Condo with Private Sauna
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
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 Cavendish
4.97 out of 5 average rating, 143 reviewsThe Cozy Little Red Cabin
Cabin in Woodstock
4.95 out of 5 average rating, 198 reviewsHideaway Cabin by the Stream on 27 Acres
Cabin in Topsham
5 out of 5 average rating, 259 reviewsPine Cabin, Galusha Hill Farm, incredible view!
Guesthouse in Groton
4.97 out of 5 average rating, 258 reviewsGroton Forest Retreat
Rental unit in Andover
4.98 out of 5 average rating, 408 reviewsPrivate Hilltop farm apartment
Home in Danby
4.96 out of 5 average rating, 214 reviewsComfortable farmhouse with stunning views
Rental unit in Montpelier
4.87 out of 5 average rating, 662 reviewsEntire 2nd Floor Walk to Montpelier
Home in Corinth
4.99 out of 5 average rating, 294 reviewsDawnside - Green Mtns Home with White Mtns View
Family-friendly home rentals with a pool
Guesthouse in Ticonderoga
5 out of 5 average rating, 210 reviewsChilson Brook Alpacas
Rental unit in Barre
4.94 out of 5 average rating, 161 reviewsRelax in Recreation Paradise!
Condo in Killington
4.93 out of 5 average rating, 88 reviewsCozy 1-bed, Mountain Green Resort - Killington, VT
Condo in Killington
4.74 out of 5 average rating, 65 reviewsKillington Vermont Luxury 2 bed condo
Condo in Killington
4.95 out of 5 average rating, 98 reviews⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
Condo in Warren
4.97 out of 5 average rating, 119 reviewsTWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
Home in Chittenden
4.91 out of 5 average rating, 87 reviewsComfortable, relaxing large country home
Townhouse in Killington
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
G$29,189 GYD 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
Destinations to explore
- Burlington Vacation rentals
- Lake George Vacation rentals
- Lake Placid Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Vermont
- Family-friendly rentals Vermont
- Family-friendly rentals New York
- Family-friendly rentals New Hampshire
- Rentals with a patio Pittsfield
- House rentals Pittsfield
- Rentals with a fire pit Pittsfield
- Pet-friendly rentals Pittsfield
- Rentals with a fireplace Pittsfield
- Rentals with a washer and dryer Pittsfield
- Rentals with outdoor seating Pittsfield
- Monthly Rentals Pittsfield
- Family-friendly rentals Rutland 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