Holiday rentals in Sheffield

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Top-rated holiday rentals in Sheffield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
Escape to a private acre of forest in the Berkshires near Great Barrington. Our large post and beam log cabin has been updated with all the modern essentials like WiFi, streaming channels, open kitchen, outdoor deck, gym/yoga studio, ping pong table and a screened porch for those beautiful warm evenings. If you have young children, you will love the separate playroom stocked with toys, books and games. For hikers, the AT is 1 hour hike from the front porch. 2:15 from NYC and 2:30 from BOS
23–30 Jun
₹41,528 per night
4.81 out of 5 average rating, 245 reviews
Guest favourite
Loft in Great Barrington
The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.
22–29 Apr
₹11,363 per night
4.99 out of 5 average rating, 295 reviews
Guest favourite
Flat in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
29 Aug – 5 Sep
₹7,663 per night
4.93 out of 5 average rating, 247 reviews

Popular amenities for Sheffield holiday rentals

Stay near Sheffield's top sights

The Pass | Marijuana Dispensary in the Berkshires3 locals recommend
Race Brook Lodge5 locals recommend
Bartholomew's Cobble Reservation45 locals recommend
The Marketplace Kitchen and Cafe20 locals recommend
Bash Bish Brew & Que4 locals recommend
The Bridge Restaurant7 locals recommend

Other great holiday rentals in Sheffield

Guest favourite
Home in Sheffield
A Private Peninsula Retreat In The Berkshires!
23 Feb – 2 Mar
₹29,366 per night
4.93 out of 5 average rating, 111 reviews
Guest favourite
Guest house in Lenox
The Granary at House on Golden Hill
28 Apr – 5 May
₹8,709 per night
4.94 out of 5 average rating, 267 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
30 Nov – 7 Dec
₹15,856 per night
4.94 out of 5 average rating, 129 reviews
Guest favourite
Cottage in Great Barrington
Artist Cottage
10–17 Jun
₹14,983 per night
4.93 out of 5 average rating, 234 reviews
Guest favourite
Cottage in Hillsdale
Cozy Cottage Catamount, Berkshires Walk to Brewery
11–18 Jul
₹9,916 per night
4.94 out of 5 average rating, 171 reviews
Guest favourite
Cottage in Copake Falls
Beautiful cottage in Copake Falls
9–16 Jun
₹11,171 per night
4.9 out of 5 average rating, 313 reviews
Guest favourite
Farm stay in Ancram
Relaxing secluded stay with loving social animals.
7–14 Oct
₹11,584 per night
4.95 out of 5 average rating, 257 reviews
Guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
24–31 Dec
₹18,654 per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Sheffield
Walt's Place-Your Family Getaway
9–16 Aug
₹27,395 per night
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
17–24 Feb
₹17,056 per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
3–10 Jun
₹12,496 per night
5.0 out of 5 average rating, 59 reviews
Superhost
Home in Sheffield
Charming Berkshires Cottage by Evergreen Home
10–17 Apr
₹12,816 per night
4.82 out of 5 average rating, 65 reviews

Quick stats about holiday rentals in Sheffield

Total rentals

90 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

3.7T reviews

Nightly prices starting at

₹8,291 before taxes and fees

Destinations to explore