House vacation rentals in Sheffield
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Top-rated house rentals in Sheffield
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Oct 16 – 23
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 Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Nov 12 – 19
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
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Sep 20 – 27
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
Sep 22 – 29
Weekly house rentals
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
Oct 2 – 9
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Mar 30 – Apr 6
Home in Copake
4.96 out of 5 average rating, 172 reviewsLakefront +views +skiing +bbq +firepit +games
Apr 26 – May 3
Home in Dalton
4.88 out of 5 average rating, 113 reviewsThe Yellow House
Feb 16 – 23
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Mar 22 – 29
Home in Ancramdale
4.99 out of 5 average rating, 159 reviewsBeautiful Weekend Coming Up & Sunsets On the Lake
Apr 24 – May 1
Home in Sheffield
4.99 out of 5 average rating, 82 reviewsBelle Meade
Nov 3 – 10
Home in Sheffield
5.0 out of 5 average rating, 26 reviewsThe Kellogg House in the Heart of The Berkshires
Dec 14 – 21
Private house rentals
Home in Copake
4.92 out of 5 average rating, 38 reviewsYellow Door House
Aug 6 – 13
Home in Sheffield
4.9 out of 5 average rating, 68 reviewsBerkshires Walk to Winery, Distillery & Brewery
Nov 23 – 30
Home in Sheffield
5.0 out of 5 average rating, 11 reviewsCharming Country House with a Hot Tub
Nov 8 – 15
Home in Great Barrington
5.0 out of 5 average rating, 8 reviewsCharming Cottage - Walk To Town
May 3 – 10
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
Nov 27 – Dec 4
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Jan 4 – 11
Home in Great Barrington
5.0 out of 5 average rating, 9 reviewsCountry Castle-Complete privacy-minutes from town
May 8 – 15
Home in Great Barrington
5.0 out of 5 average rating, 18 reviewsNewly remodeled home with all the modern amenities
Mar 23 – 30
Quick stats about house rentals in Sheffield
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
$120 before taxes and fees
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