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Vacation rentals in Sheffield

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Top-rated vacation rentals in Sheffield

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

Private Berkshire Barn Apartment
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Private Berkshire Barn ApartmentA private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.
Hideaway with Spectacular Berkshire Views
SUPERHOST
Entire rental unit · 3 guests · 2 beds · 1 bath
Hideaway with Spectacular Berkshire ViewsLocated on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.
Winter Eco Mongolian Yurt in the Berkshires
SUPERHOST
Yurt · 2 guests · 1 bed · 1 bath
Winter Eco Mongolian Yurt in the BerkshiresAuthentic off-the-grid Mongolian yurt with windows, skylight, and wood stove. This is the Winter Listing. THERE IS NO RUNNING WATER OFF-SEASON. Our lovely 20 foot (approx 300sf) yurt is located in a semi-private corner of our property, adjacent to the woods. It is one large open room with an outbuilding toilet. On a clear night, stargaze from the comfort of the (very comfortable) bed. On a rainy night, enjoy the sound of the rain on the roof.

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Popular amenities for Sheffield vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Sheffield

SUPERHOST
  1. Entire residential home
  2. Sheffield
A Private Peninsula Retreat In The Berkshires!
SUPERHOST
  1. Entire guest suite
  2. Canaan
Walk to Brewery in Historic Railroad Depot
  1. Entire serviced apartment
  2. Canaan
Cozy 1 bedroom apartment with deck & fireplace.
  1. Entire guest suite
  2. Mount Washington
Fall/Winter Spa Sanctuary with Trail System
SUPERHOST
  1. Entire cottage
  2. Great Barrington
Newly built cottage on working farm
SUPERHOST
  1. Entire loft
  2. Great Barrington
The Old Red Barn
SUPERHOST
  1. Entire residential home
  2. Great Barrington
Classic Cottage in Sun-Drenched Meadow in Great Barrington
  1. Entire cottage
  2. Sheffield
Charming Ashley Falls Cottage Retreat
SUPERHOST
  1. Entire residential home
  2. Great Barrington
Victorian Modern, Walk to Town
SUPERHOST
  1. Entire residential home
  2. Canaan
Litchfield County Retreat
  1. Entire bungalow
  2. Sheffield
Cheerful 2-bedroom bungalow in the Berkshires
SUPERHOST
  1. Entire residential home
  2. Egremont
The Berkshires Mountain Terrace LUX Home Sleeps 10