Family-friendly vacation rentals in Sheffield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Sheffield
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Sep 6 – 13
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Mar 22 – 29
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
Sep 12 – 19
Cabin in Saugerties
4.86 out of 5 average rating, 171 reviewsContainer Cabin in the Catskills (Field)
Dec 18 – 25
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
Jun 5 – 12
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Oct 11 – 18
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
Jan 19 – 26
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
Jun 10 – 15
Family- and pet-friendly home rentals
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
May 31 – Jun 7
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Dec 3 – 10
Cottage in Red Hook
4.98 out of 5 average rating, 598 reviewsbright serene + spacious barn
Dec 6 – 13
Loft in East Nassau
4.99 out of 5 average rating, 153 reviewsDog Friendly Farm Spring bird watching
Aug 29 – Sep 5
Farm stay in West Simsbury
4.95 out of 5 average rating, 430 reviewsFlamig Farm Staycation
Nov 7 – 14
Cottage in Pine Plains
5.0 out of 5 average rating, 132 reviewsPatchin Mills Quaint Country Cottage
Mar 26 – Apr 2
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Jul 4 – 11
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Mar 29 – Apr 5
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Nov 12 – 19
Home in New Paltz
4.98 out of 5 average rating, 435 reviewsmidcentury modern in ground pool walk 2 trail/town
Nov 26 – Dec 3
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Oct 16 – 23
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Aug 3 – 10
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct 27 – Nov 3
Home in Litchfield
4.93 out of 5 average rating, 162 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 8 – 15
Townhouse in Hudson
4.94 out of 5 average rating, 193 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
Oct 6 – 13
Quick stats about vacation rentals that are family-friendly in Sheffield
Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
2.4K reviews
Nightly prices starting at
$140 before taxes and fees
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