Sheffield Vacation Rentals, Houses & More


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Great rentals within 20 miles that match your search

1 / 14

Newly Renovated Lakefront Getaway on Robinson Pond

  • 3
  • 6
  • 3 nights min

$201

Details

1 / 18

Hillhouse Log Cabin

  • 3
  • 13
  • 2 nights min

$425

Details

1 / 11

Berkshires Spacious Comfortable Charming Farmhouse

  • 3
  • 8
  • 2 nights min

$300

Details

1 / 12

little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 16

TAKE ME HOME, COUNTRY ROADS

  • 3
  • 6
  • 4 nights min

$226

Details

1 / 2

chestnut lodge Queens Room

  • 1
  • 2
  • 2 nights min

$176

Details

1 / 4

Exclusive Rental in Beautiful Amenia!

  • 3
  • 6
  • 30 nights min

$134

Details

1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$201

Details

1 / 37

Charming 2+2 Lakeside Cottage on Best Lake in CT

  • 2
  • 4
  • Min stay varies

$181

Details

1 / 20

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

  • 3
  • 6
  • 7 nights min

$501

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 32

Escape to the Berkshires!

  • 4
  • 8
  • 2 nights min

$275

Details

1 / 15

S. Berkshires Mountain Treehouse • Views • Privacy

  • 2
  • 4
  • 14 nights min

$243

Details

1 / 27

Copake Lakeview Ranch

  • 3
  • 12
  • Min stay varies

$190

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$651

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 21

Serene Lakefront Cottage

  • 2
  • 4
  • Min stay varies

$150

Details

1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$376

Details

1 / 5

Cozy Modern Condo for the Berkshires

  • 2
  • 6
  • 1 night min

$176

Details

1 / 25

Luxury and Amenities in a Stunning Rustic Setting

  • 4
  • 14
  • Min stay varies

$357

Details

1 / 20

Renovated Barn

  • 3
  • 6
  • Min stay varies

$63

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 13

Short Walk to Lake, Peaceful Getaway, Scenic Views

  • 3
  • 6
  • 2 nights min

$171

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$201

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 27

Enchanted Cottage on Babbling Brook

  • 3
  • 6
  • Min stay varies

$250

Details

1 / 6

Berkshires on the Pond

  • 2
  • 2
  • 4 nights min

$125

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$501

Details

1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$145

Details

1 / 22

Berkshire Getaway at 'Tofu'S Retreat'

  • 3
  • 6
  • Min stay varies

$144

Details

1 / 24

Perfect Getaway for Body, Mind and Soul

  • 3
  • 5
  • 7 nights min

$237

Details

1 / 11

The Cottage at Great Falls

  • 2
  • 4
  • 2 nights min

$201

Details

1 / 20

Berkshire Farmhouse Vacation

  • 5
  • 12
  • Min stay varies

$275

Details

1 / 48

Total Privacy! Tanglewood Retreat With Berkshire Views!

  • 5
  • 14
  • 2 nights min

$600

Details

1 / 13

Designer Loft Style Residence

  • 3
  • 6
  • 7 nights min

$450

Details

1 / 10

Apple Cottage

  • 3
  • 8
  • 1 night min

$376

Details

1 / 19

Restored Horse Barn On 13 Acres With Private Pond

  • 4
  • 10
  • 4 nights min

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