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Best Berkshires Apartments on Holiday Lettings - Vacation rentals

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732 Vacation rentals

Vacation home in Berkshires

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $859 / night

$5,153 / week

1 / 22

Vacation home in Becket

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $171 / night

$1,140 / week

1 / 13

Vacation apartment in Berkshires

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

from $229 / night

$1,374 / week

1 / 21

Berkshires Vacation home rental

Monterey house

  • 2 bathrooms
  • sleeps 7

from $205 / night

$1,432 / week

1 / 12

North Adams Vacation apartment rental

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $338 / night

$1,718 / week

1 / 12

Vacation home in Berkshires

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $172 / night

$1,203 / week

1 / 0

Vacation home in Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $401 / night

$2,806 / week

1 / 26

Vacation home in Williamstown

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

from $195 / night

$1,363 / week

1 / 0

Vacation farmhouse in Berkshires

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $172 / night

$1,031 / week

1 / 4

Vacation farmhouse in Berkshires

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $172 / night

$1,031 / week

1 / 4

Great Barrington Vacation home rental

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $172 / night

$1,088 / week

1 / 14

Berkshires Vacation home rental

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $229 / night

$1,374 / week

1 / 6

Berkshires Vacation hotel apartment rental

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $115 / night

$801 / week

1 / 1

Vacation home in Berkshires

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $859 / night

$3,435 / week

1 / 7

Home rental in Berkshires

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $172 / night

$1,203 / week

1 / 17

Vacation home in Berkshires

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $682 / night

$3,779 / week

1 / 23

Vacation studio in Berkshires

Hancock studio

  • Studio
  • 1 bathroom
  • sleeps 4

from $132 / night

$920 - $1,988 / week

1 / 67

Vacation home with golf nearby in Berkshires

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

from $818 / night

$5,725 / week

1 / 18

Vacation cottage rental

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $274 / night

$1,831 / week

1 / 18

Vacation home in Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $344 / night

$2,405 / week

1 / 12

Vacation home rental

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $327 / night

$2,290 / week

1 / 20

Vacation condo in Hancock

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $258 / night

$1,804 / week

1 / 14

Vacation home in Berkshires

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $458 / night

$3,206 / week

1 / 31

Home rental in Berkshires

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $315 / night

$1,374 / week

1 / 20

Berkshires Vacation condo rental

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $262 / night

$1,832 / week

1 / 6

Vacation home in Hinsdale

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $218 / night

$1,168 - $1,248 / week

1 / 10

Vacation home rental

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

from $298 / night

$1,775 - $3,579 / week

1 / 20

Vacation apartment in Berkshires

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $373 / night

$2,605 - $3,407 / week

1 / 12

Sheffield Vacation home rental

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $686 / night

$4,801 / week

1 / 74

Ski condo to rent in Berkshires

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $260 / night

$1,489 / week

1 / 39

Vacation home in Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $2,863 / night

$34,302 / week

1 / 4

Vacation condo rental

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $430 / night

$3,006 / week

1 / 16

Stockbridge Vacation home rental

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $802 / night

$2,806 - $4,729 / week

1 / 19

Vacation home in Berkshires

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $744 / night

$5,202 / week

1 / 58

Vacation home with swimming pool in Lee

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from $659 / night

$4,609 / week

1 / 91

Vacation home in Monterey

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $573 / night

$4,008 / week

1 / 23

Vacation home in Berkshires

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $572 / night

$4,000 / week

1 / 25

Vacation apartment in East Otis

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $126 / night

$802 / week

1 / 20

Lanesborough Vacation home rental

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

from $795 / night

$4,574 / week

1 / 18

Vacation home in Great Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $572 / night

$4,000 / week

1 / 52

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