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Best Vacation Rentals in Sheffield - Holiday Lettings - Cabins

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25 Vacation rentals

Sheffield Vacation home rental

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $686 / night

$4,801 / week

1 / 74

Sheffield ski home to rent.

Sheffield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $283 / night

$1,981 / week

1 / 30

Vacation villa rental

Sheffield villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 30

from $1,728 / night

$12,096 / week

1 / 30

Sheffield ski home to rent.

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $187 / night

$1,309 / week

1 / 19

Ski home to rent in Sheffield

Sheffield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $756 / night

$5,292 / week

1 / 30

Sheffield Vacation home rental

Sheffield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from $350 / night

$2,450 / week

1 / 18

Sheffield ski home to rent.

Sheffield house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

from $608 / night

$4,256 / week

1 / 23

Ski home to rent in Sheffield

Sheffield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from $414 / night

$2,898 / week

1 / 30

Vacation home rental

Sheffield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $279 / night

$1,953 / week

1 / 30

Ski home to rent in Sheffield

Sheffield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $255 / night

$1,785 / week

1 / 22

Sheffield ski home to rent.

Sheffield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 16

from $483 / night

$3,381 / week

1 / 30

Ski home to rent in Sheffield

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $274 / night

$1,918 / week

1 / 30

Vacation home rental

Sheffield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $250 / night

$1,750 / week

1 / 30

Vacation home rental

Sheffield house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $150 / night

$1,050 / week

1 / 30

Sheffield ski home to rent.

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $599 / night

$4,193 / week

1 / 30

Vacation home in Sheffield

Sheffield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $217 / night

$1,519 / week

1 / 30

Sheffield ski home to rent.

Sheffield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $223 / night

$1,561 / week

1 / 26

Ski home to rent in Sheffield

Sheffield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $203 / night

$1,421 / week

1 / 18

Vacation home in Sheffield

Sheffield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $692 / night

$4,844 / week

1 / 30

Ski home to rent in Sheffield

Sheffield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,055 / night

$7,385 / week

1 / 30

Sheffield Vacation home rental

Sheffield house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $137 / night

$959 / week

1 / 17

Sheffield ski home to rent.

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from $285 / night

$1,995 / week

1 / 30

Sheffield ski home to rent.

Sheffield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $410 / night

$2,870 / week

1 / 30

Vacation home rental

Sheffield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $80 / night

$560 / week

1 / 10

Ski home to rent in Sheffield

Sheffield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $100 / night

$700 / week

1 / 21

Great rentals within 20 miles that match your search

Vacation farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $172 / night

$1,031 / week

1 / 4

Vacation farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $172 / night

$1,031 / week

1 / 4

Lee Vacation apartment rental

Lee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $201 / night

$974 / week

1 / 13

Vacation home in Copake

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from $287 / night

$2,004 / week

1 / 14

Falls Village Vacation cottage accommodation

Falls Village cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $275 / night

$1,924 - $2,966 / week

1 / 18

Vacation home rental

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

from $298 / night

$1,775 - $3,579 / week

1 / 20

Home rental in Becket

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $315 / night

$1,374 / week

1 / 20

Vacation home in Lee

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $859 / night

$3,435 / week

1 / 7

Great Barrington Vacation home rental

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $172 / night

$1,088 / week

1 / 14

Log cabin rental in Hillsdale

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $229 / night

$1,203 / week

1 / 31

Cottage rental in Salisbury

Salisbury cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $207 / night

$1,443 / week

1 / 37

Vacation apartment in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

from $229 / night

$1,374 / week

1 / 21

Vacation home in Stockbridge

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $859 / night

$5,153 / week

1 / 22

Monterey Vacation home rental

Monterey house

  • 2 bathrooms
  • sleeps 7

from $205 / night

$1,432 / week

1 / 12

Vacation home in Hillsdale

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from $1,145 / night

$8,015 / week

1 / 48