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
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Feb 9 – 16
Home in Great Barrington
4.96 out of 5 average rating, 213 reviewsJaw dropping mountain & lake views
Nov 18 – 25
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
May 7 – 14
Home in Egremont
4.93 out of 5 average rating, 256 reviewsModern Farm House 5 minutes from Great Barrington
Apr 6 – 13
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
Mar 14 – 21
Home in Great Barrington
4.95 out of 5 average rating, 114 reviewsThe Hideaway: Berkshire Home - village of Egremont
Oct 4 – 11
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Nov 21 – 28
Home in Millerton
4.96 out of 5 average rating, 113 reviewsVacation Home In Millerton
Mar 26 – Apr 2
Kid-friendly apartment rentals
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Nov 22 – 29
Apartment in Great Barrington
4.95 out of 5 average rating, 131 reviewsGB Eclectic Victorian
Apr 2 – 9
Apartment in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
Sep 29 – Oct 6
Apartment in Millerton
4.8 out of 5 average rating, 230 reviewsGardens Galore and Village Whimsy Retreat
Mar 8 – 15
Apartment in Hudson
4.95 out of 5 average rating, 100 reviewsRestored 19th century farm house apartment
Nov 4 – 11
Apartment in Plainfield
4.97 out of 5 average rating, 238 reviewsSunny, light filled loft in 1873 Colonial
Mar 7 – 14
Apartment in Petersburg
4.85 out of 5 average rating, 149 reviewsThe Beer Diviner Brewery Apartment
Feb 22 – Mar 1
Apartment in Winchester
4.91 out of 5 average rating, 340 reviewsGateway to the Berkshires
Mar 14 – 21
Kid-friendly condo rentals
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Oct 29 – Nov 5
Condo in Poughkeepsie
4.97 out of 5 average rating, 224 reviewsSpacious and stylish entire one bedroom apartment.
Jul 3 – 10
Condo in Middletown
4.97 out of 5 average rating, 103 reviewsEntire place to yourself Cromwell/Middletown Line
Feb 17 – 24
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
Jun 16 – 23
Condo in Albany
4.89 out of 5 average rating, 161 reviewsElegant, spacious studio apt in historic mansion
Sep 4 – 11
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 30 – Jun 6
Condo in Kingston
4.91 out of 5 average rating, 104 reviewsCozy home walking distance to cafés & waterfront
Jul 13 – 20
Condo in New Britain
4.87 out of 5 average rating, 39 reviewsBeautiful Space All For You!
Oct 23 – 30
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
ﺩ.ﺇ441 before taxes and fees
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