Kid-friendly vacation rentals in Pittsfield
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Pittsfield
Guests agree: these kid-friendly rentals 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 kid-friendly rentals
Kid-friendly house rentals
Home in Stockbridge
4.97 out of 5 average rating, 104 reviewsGreek Revival Farmhouse
Home in Otis
4.94 out of 5 average rating, 142 reviewsBerkshires hideaway! Hikes & serenity near lake
Home in Ancram
4.82 out of 5 average rating, 109 reviewsSecluded Post-And-Beam Retreat
Home in Cohoes
5 out of 5 average rating, 115 reviewsCheerful, quiet 3 bedroom home
Home in Pittsfield
4.94 out of 5 average rating, 144 reviewsCantabile life in the Berkshires
Home in Huntington
4.91 out of 5 average rating, 128 reviewsPrivate house on the River
Home in Dover
4.87 out of 5 average rating, 237 reviewsMt Snow retreat, ski & summer
Home in Wilmington
4.91 out of 5 average rating, 139 reviewsMartin Ski Barn - 4BR Ski House, 15 min to Mt Snow
Kid-friendly apartment rentals
Rental unit in Lenox Dale
4.91 out of 5 average rating, 127 reviewsCharming 2BD apartment.
Rental unit in Shelburne Falls
4.86 out of 5 average rating, 402 reviewsBig, sunny 1893 flat steps from Bridge of Flowers
Rental unit in Albany
4.84 out of 5 average rating, 127 reviewsGarden Apartment in Ctr. Square: Monthly Discounts
Rental unit in Hudson
4.93 out of 5 average rating, 275 reviewsChic Hudson Apartment - In the heart of Hudson, NY
Rental unit in Westfield
4.8 out of 5 average rating, 131 reviewsPrivate entry studio
Rental unit in Catskill
4.97 out of 5 average rating, 237 reviewsAbove SpringRise
Rental unit in Saugerties
4.94 out of 5 average rating, 129 reviewsUPSTATE OF MIND ~ The ❤️ of the Catskills.
Rental unit in Albany
4.94 out of 5 average rating, 241 reviewsCharming Garden Apartment in Center Square
Kid-friendly condo rentals
Condo in West Dover
4.75 out of 5 average rating, 132 reviewsBeautiful condo 2.5 miles from Mount Snow
Condo in Dover
4.9 out of 5 average rating, 30 reviewsCozy Mnt Snow Condo - *4 Min walk to Lift*
Condo in Dover
4.99 out of 5 average rating, 105 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Condo in Albany
4.9 out of 5 average rating, 220 reviewsElegant, spacious studio apt in historic mansion
Condo in Hancock
4.85 out of 5 average rating, 142 reviewsCozy Condo @ Jiminy Peak
Condo in Dover
4.84 out of 5 average rating, 157 reviewsMount Snow Close, Great Price, Lots of Room
Condo in Dover
5 out of 5 average rating, 41 reviewsGorgeous , Ski/ Mountain View 2 bedroom, 2 bath
Quick stats about vacation rentals that are kid-friendly in Pittsfield
Total rentals
40 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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