House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Sheffield
House rentals with a pool
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
25 Jan – 1 Feb
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
22–29 Oct
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
14–21 Jul
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
8–15 Dec
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
29 Dec – 5 Jan
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
23–30 Sep
Weekly house rentals
Home in Copake
4.96 out of 5 average rating, 172 reviewsLakefront +views +skiing +bbq +firepit +games
8–15 Sep
Home in Rhinebeck
4.91 out of 5 average rating, 255 reviewsArchitectural wonder in the woods
15–22 Oct
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
6–13 Jun
Home in Ancramdale
4.99 out of 5 average rating, 159 reviewsBeautiful Weekend Coming Up & Sunsets On the Lake
7–14 Mar
Home in Sheffield
5.0 out of 5 average rating, 26 reviewsThe Kellogg House in the Heart of The Berkshires
3–10 Dec
Home in Sheffield
4.99 out of 5 average rating, 82 reviewsBelle Meade
11–18 Oct
Home in Sheffield
4.91 out of 5 average rating, 76 reviewsHouse Among Trees - A Perfect Getaway
26 Jul – 2 Aug
Home in Sheffield
4.98 out of 5 average rating, 46 reviewsWalt's Place-Your Family Getaway
24–31 Oct
Private house rentals
Home in Sheffield
4.9 out of 5 average rating, 69 reviewsBerkshires Walk to Winery, Distillery & Brewery
7–14 May
Home in Sheffield
5.0 out of 5 average rating, 11 reviewsCharming Country House with a Hot Tub
13–20 Nov
Home in Great Barrington
5.0 out of 5 average rating, 68 reviewsGranite Ledge, Modern home in a unique setting
12–19 Jan
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
9–16 Jun
Home in Great Barrington
5.0 out of 5 average rating, 9 reviewsCountry Castle-Complete privacy-minutes from town
5–12 Jun
Home in Great Barrington
5.0 out of 5 average rating, 9 reviewsCharming Cottage - Walk To Town
13–20 May
Home in Hillsdale
5.0 out of 5 average rating, 23 reviewsEnjoy all 4 Seasons
12–19 Jan
Home in Great Barrington
4.87 out of 5 average rating, 47 reviewsCountryside Calm. Proximity to Berkshires' Best!
12–19 Jun
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
1.9T reviews
Nightly prices starting at
₹10,004 before taxes and fees
Destinations to explore
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