Sheffield Vacation Rentals, Houses & More


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Great rentals within 20 miles that match your search

1 / 13

Garfield House

  • 2
  • 6
  • 2 nights min

$176

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 11

Riverwood - Cozy Carriage House in the Woods

  • 1
  • 2
  • 2 nights min

$166

Details

1 / 16

Berkshires House, 40 wooded acres, Lake Frontage

  • 3
  • 8
  • 1 night min

$176

Details

1 / 18

Spacious wooded home

  • 4
  • 12
  • 3 nights min

$196

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 7

Deluxe New Home, 2 Master Suites, Tanglewood Area

  • 5
  • 12
  • 3 nights min

$750

Details

1 / 6

Berkshires on the Pond

  • 2
  • 2
  • 4 nights min

$125

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$651

Details

1 / 23

Spacious Lakeside Berkshire Home

  • 4
  • 10
  • Min stay varies

$401

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 24

Perfect Getaway for Body, Mind and Soul

  • 3
  • 5
  • 7 nights min

$237

Details

1 / 18

Restored 1940s Cabin 30 Mile Views

  • 2
  • 5
  • 2 nights min

Inquire for Rates

Details

1 / 16

Olde York Farm Distillery Suite

  • 2
  • 6
  • 1 night min

$250

Details

1 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

1 / 10

Country Victorian Serenity in the Berkshires

  • 4
  • 6
  • 7 nights min

$229

Details

1 / 24

Beautiful Lakefront Berkshire Rental

  • 5
  • 6
  • 7 nights min

$351

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 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$176

Details

1 / 15

Outdoor getaway hunting,fishing,skiing..relaxation

  • 3
  • 9
  • 2 nights min

$191

Details

1 / 37

Charming 2+2 Lakeside Cottage on Best Lake in CT

  • 2
  • 4
  • Min stay varies

$181

Details

1 / 15

Newly Renovated Vacation Home near Catamount Ski

  • 3
  • 10
  • Min stay varies

$300

Details

1 / 32

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$129

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$501

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$134

Details

1 / 12

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

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 32

Escape to the Berkshires!

  • 4
  • 8
  • 2 nights min

$275

Details

1 / 13

Short Walk to Lake, Peaceful Getaway, Scenic Views

  • 3
  • 6
  • 2 nights min

$171

Details

1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$326

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

Inquire for Rates

Details

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