
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

Top of the World! Jacuzzi! Private Hiking Trails!

Macintosh Hill Farm

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Okemo Ski Chalet with Hot Tub

Killington area home - 4-seasons & hot tub

4br, 3ba with 2 master bedrooms, Sauna, Hot Tub

Killington ski house winter MTbike -new jacuzzi

#45 Luxury Ski & Summer Condo with Private Sauna
Family- and pet-friendly home rentals

Large New England Home w/ Gorgeous Mountain Views

Downtown Middlebury 3 BR Home - Walk Everywhere!

So Vt Cabin Mt Tabor Treasure

The McKinley House

Exquisite Green Mountain Loft Haven

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

The Green Mountain Chalet

Henrietta’s Hideaway-Walk Downtown!
Family-friendly home rentals with a pool

Relax in Recreation Paradise!

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Moon Valley Country Retreat no clean fee pets yes

*Killington Summer Rental: 3 Bdrm, 2 Bth*

Ski, Ride, Walk On/Off Condo On Pico at Killington

Serene Top Floor Condo (resort style amenities)

Pico discounted 1 bedroom 1 nght Ok shuttle
Quick stats about holiday rentals that are family-friendly in Pittsfield
Total rentals
60 properties
Nightly prices starting at
€ 138 before taxes and fees
Total number of reviews
2.4K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
- Montreal Holiday rentals
- Boston Holiday rentals
- Hudson Valley Holiday rentals
- Cape Cod Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Québec City Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Rentals with a washing machine and dryer Pittsfield
- Rentals with outdoor seating Pittsfield
- Rentals with a firepit Pittsfield
- Pet-friendly rentals Pittsfield
- Rentals with a fireplace Pittsfield
- House rentals Pittsfield
- Rentals with a patio Pittsfield
- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- 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
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Cochran's Ski Area
- Country Club of Vermont
- Mount Sunapee Resort
- Adirondack Extreme Adventure Course
- Vermont National Country Club
- Lincoln Peak Vineyard
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Ekwanok Country Club
- Cozy Cottages & Otter Valley Winery
- Fort Ticonderoga
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Fox Run Golf Club
- Whaleback Mountain
- Killington Adventure Center
- Storrs Hill Ski Area