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Vacation home rental

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

from $298 / night

$1,775 - $3,579 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation home rental

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $327 / night

$2,290 / week

1 / 20

Williamstown Vacation condo rental

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $262 / night

$1,832 / week

1 / 6

Vacation home in Copake

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from $287 / night

$2,004 / week

1 / 14

Vacation apartment in Lee

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $373 / night

$2,605 - $3,407 / week

1 / 12

Vacation log cabin rental

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

from $487 / night

$1,890 - $2,090 / week

1 / 18

Vacation condo rental

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $430 / night

$3,006 / week

1 / 16

Great Barrington Vacation home rental

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $172 / night

$1,088 / week

1 / 14

Vacation home in Hancock

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $2,863 / night

$34,302 / week

1 / 4

Vacation home in Stephentown

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from $687 / night

$2,863 - $3,344 / week

1 / 4

Columbiaville Vacation home rental

Columbiaville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $287 / night

$1,890 / week

1 / 16

Vacation home in Hinsdale

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $218 / night

$1,168 - $1,248 / week

1 / 10

Vacation home with golf nearby in Lee

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

from $818 / night

$5,725 / week

1 / 18

Vacation condo in Hancock

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $258 / night

$1,804 / week

1 / 14

Vacation home in Spencertown

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $153 / night

$1,069 / week

1 / 14

Vacation home in Monterey

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $573 / night

$4,008 / week

1 / 23

East Chatham Vacation home rental

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,030 / night

$7,206 / week

1 / 42

Ski condo to rent in Hancock

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $260 / night

$1,489 / week

1 / 39

Hillsdale Vacation home rental

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $281 / night

$1,718 / week

1 / 13

Old Chatham Vacation villa rental

Old Chatham villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 16

from $1,374 / night

$9,618 / week

1 / 38

Home rental in Nassau

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $298 / night

$2,004 - $2,645 / week

1 / 8

Log cabin rental in Hillsdale

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $229 / night

$1,203 / week

1 / 31

Vacation condo with shared pool in South Lee

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $70 / night

$489 / week

1 / 15

Vacation condo with shared pool in South Lee

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $81 / night

$561 / week

1 / 15

Ski b&b to rent in Stephentown

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $109 / night

$630 / week

1 / 23

Lanesborough Vacation home rental

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

from $795 / night

$4,574 / week

1 / 18

Vacation home in Craryville

Craryville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $344 / night

$2,405 / 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 Ashley Falls

Ashley Falls house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $915 / night

$6,404 / week

1 / 46

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 Great Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $572 / night

$4,000 / week

1 / 52

Vacation home in Stockbridge

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $458 / night

$3,206 / week

1 / 31

Vacation home in Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $343 / night

$2,397 / week

1 / 25

Vacation home in Lee

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $744 / night

$5,202 / week

1 / 58

Sheffield Vacation home rental

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $686 / night

$4,801 / week

1 / 74