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
Home in Pittsfield
4.83 out of 5 average rating, 221 reviewsKillington area home - 4-seasons & hot tub
31 Oct – 7 Nov
Apartment in Killington
4.77 out of 5 average rating, 282 reviewsSerene Killington Condo (resort style amenities)
24–31 Jul
Yurt in Randolph
4.96 out of 5 average rating, 386 reviews4 Season Lower Yurt Stay on VT Homestead
11–18 Oct
Chalet in Killington
4.9 out of 5 average rating, 159 reviewsClose to Mountain and walk to restaurants!
1–8 Jul
Home in Killington
4.88 out of 5 average rating, 215 reviewsTanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ
14–21 May
Chalet in Killington
5.0 out of 5 average rating, 117 reviewsLuxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard
29 Oct – 5 Nov
Apartment in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
28 Aug – 4 Sep
Chalet in Killington
4.82 out of 5 average rating, 234 reviewsKillington Chalet - Hot Tub, Sauna, Boot Dryer
13–20 Feb
Family- and pet-friendly home rentals
Cottage in Lincoln
4.87 out of 5 average rating, 857 reviewsThe Barn at North Orchard, Near Middlebury
9–16 Dec
Guest house in Granville
4.9 out of 5 average rating, 786 reviewsMoon Valley Country Retreat no clean fee pets yes
9–16 Mar
Home in Rochester
4.94 out of 5 average rating, 181 reviewsThe McKinley House
3–10 Feb
Cabin in Bethel
4.94 out of 5 average rating, 386 reviewsRustic and Cozy Vermont Getaway at Sugarwood Cabin
14–21 Feb
Guest house in Hartland
4.95 out of 5 average rating, 913 reviewsYurt In The Woods - Private Refuge
26 Mar – 2 Apr
Flat in Andover
4.98 out of 5 average rating, 386 reviewsPrivate Hilltop farm apartment
29 Sep – 6 Oct
Guest house in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
22–29 Nov
Home in Granville
4.95 out of 5 average rating, 107 reviewsEpic Views of the Green Mountains
Family-friendly home rentals with a pool
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
20–27 Aug
Apartment in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
27 Nov – 4 Dec
Cabin in Bridport
4.92 out of 5 average rating, 133 reviewsChamplain Valley Alpacas
12–19 Oct
Flat in Barre
4.94 out of 5 average rating, 156 reviewsRelax in Recreation Paradise!
10–17 Sep
Flat in Killington
4.92 out of 5 average rating, 119 reviewsFamily and work friendly Spa at the Woods condo
2–9 Aug
Apartment in Killington
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
12–19 Sep
Apartment in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
16–23 Apr
Apartment in Killington
4.8 out of 5 average rating, 106 reviewsKillington Escape 2 Story 2BR 2BA Main Building
27 May – 3 Jun
Quick stats about holiday rentals that are family-friendly in Pittsfield
Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
2.3K reviews
Nightly prices starting at
€ 112 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
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- Family-friendly rentals United States
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- Family-friendly rentals Vermont
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- Rentals with a fireplace Pittsfield
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- Monthly Rentals Pittsfield
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