Kid-friendly vacation rentals in Sheffield
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Sheffield
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 Sheffield kid-friendly rentals
Kid-friendly house rentals
Home in Monterey
4.93 out of 5 average rating, 118 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Home in Monterey
4.93 out of 5 average rating, 312 reviewsCharming cottage w/ gorgeous views.
Home in Sheffield
4.97 out of 5 average rating, 118 reviewsGorgeous Sheffield Home
Home in Great Barrington
4.96 out of 5 average rating, 219 reviewsJaw dropping mountain & lake views
Home in Millerton
4.96 out of 5 average rating, 123 reviewsVacation Home In Millerton
Home in Egremont
4.93 out of 5 average rating, 259 reviewsModern Farm House 5 minutes from Great Barrington
Home in New Lebanon
4.99 out of 5 average rating, 351 reviewsThe old sawmill from 1771
Home in Egremont
4.9 out of 5 average rating, 111 reviewsCozy Berkshire Cape
Kid-friendly apartment rentals
Apartment in Great Barrington
4.94 out of 5 average rating, 133 reviewsGB Eclectic Victorian
Apartment in Hudson
4.95 out of 5 average rating, 102 reviewsRestored 19th century farm house apartment
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Apartment in Millerton
4.79 out of 5 average rating, 235 reviewsGardens Galore and Village Whimsy Retreat
Apartment in Hillsdale
4.99 out of 5 average rating, 176 reviewsSerene Suite Catamount Berkshires Walk to Brewery
Apartment in Winchester
4.91 out of 5 average rating, 346 reviewsGateway to the Berkshires
Apartment in Plainfield
4.98 out of 5 average rating, 240 reviewsSunny, light filled loft in 1873 Colonial
Apartment in Shelburne Falls
4.98 out of 5 average rating, 497 reviewsIn town, newly renovated studio with private deck
Kid-friendly condo rentals
Condo in Lanesville
4.97 out of 5 average rating, 553 reviewsStylish Condo Ski on/ Ski off Hunter Mountain
Condo in Hudson
4.94 out of 5 average rating, 152 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Condo in Hunter
4.97 out of 5 average rating, 434 reviews*Great Reviews* Hunter Mtn. Clean/Close/Cozy Condo
Condo in Middletown
4.97 out of 5 average rating, 110 reviewsEntire place to yourself Cromwell/Middletown Line
Condo in Hunter
4.98 out of 5 average rating, 542 reviewsHunter Mtn Liftside Ski In/Out, Slopeside!
Condo in Windham
4.89 out of 5 average rating, 138 reviewsCozy Mountain hideaway Windham, Hunter
Condo in Windham
4.74 out of 5 average rating, 244 reviewsSummer getaway w/Pool & Tennis Court
Condo in Poughkeepsie
4.97 out of 5 average rating, 234 reviewsSpacious and stylish entire one bedroom apartment.
Quick stats about vacation rentals that are kid-friendly in Sheffield
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
$120 before taxes and fees
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