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 Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Sep 28 – Oct 5
Home in Egremont
4.93 out of 5 average rating, 256 reviewsModern Farm House 5 minutes from Great Barrington
Mar 6 – 13
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
Apr 16 – 23
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Mar 17 – 24
Home in Great Barrington
4.95 out of 5 average rating, 114 reviewsThe Hideaway: Berkshire Home - village of Egremont
Sep 23 – 30
Home in Millerton
4.96 out of 5 average rating, 115 reviewsVacation Home In Millerton
Mar 19 – 26
Home in Great Barrington
4.96 out of 5 average rating, 140 reviewsElegant Year-Round Lakeside Retreat with AC
Nov 26 – Dec 3
Home in Egremont
4.9 out of 5 average rating, 109 reviewsCozy Berkshire Cape
Mar 15 – 22
Kid-friendly apartment rentals
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Feb 19 – 26
Apartment in Millerton
4.8 out of 5 average rating, 231 reviewsGardens Galore and Village Whimsy Retreat
Jan 23 – 30
Apartment in Great Barrington
4.95 out of 5 average rating, 131 reviewsGB Eclectic Victorian
Dec 11 – 18
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Oct 23 – 30
Apartment in Hudson
4.95 out of 5 average rating, 100 reviewsRestored 19th century farm house apartment
Mar 30 – Apr 6
Apartment in Hillsdale
4.99 out of 5 average rating, 171 reviewsSerene Suite Catamount Berkshires Walk to Brewery
May 18 – 25
Apartment in Winchester
4.91 out of 5 average rating, 340 reviewsGateway to the Berkshires
Mar 17 – 24
Apartment in Plainfield
4.97 out of 5 average rating, 238 reviewsSunny, light filled loft in 1873 Colonial
Oct 9 – 16
Kid-friendly condo rentals
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Jun 19 – 26
Condo in Poughkeepsie
4.97 out of 5 average rating, 224 reviewsSpacious and stylish entire one bedroom apartment.
Jun 24 – Jul 1
Condo in Middletown
4.97 out of 5 average rating, 104 reviewsEntire place to yourself Cromwell/Middletown Line
Feb 20 – 27
Condo in Albany
4.89 out of 5 average rating, 162 reviewsElegant, spacious studio apt in historic mansion
Nov 3 – 10
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Condo in Kingston
4.91 out of 5 average rating, 105 reviewsCozy home walking distance to cafés & waterfront
Sep 10 – 17
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 23 – 30
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
Aug 7 – 14
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
R2,220 ZAR before taxes and fees
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