Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

All filters (1)

Filters (1)

Clear filters

18 Vacation rentals

Applied filters (1)

Great rentals within 20 miles that match your search

Cherry Plain Vacation home rental

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $98 / night

$630 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation cottage rental

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $274 / night

$1,831 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation home in Stephentown

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from $687 / night

$2,863 - $3,344 / week

1 / 4

Great rentals within 20 miles that match your search

Vacation condo in Hancock

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $258 / night

$1,804 / week

1 / 14

Great rentals within 20 miles that match your search

Ski b&b to rent in Stephentown

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $109 / night

$630 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation home in Hawley

Hawley house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $218 / night

$1,260 / week

1 / 22

Great rentals within 20 miles that match your search

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 apartment in Lee

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $373 / night

$2,605 - $3,407 / week

1 / 12

Great rentals within 20 miles that match your search

Ski condo to rent in Hancock

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $260 / night

$1,489 / week

1 / 39

Great rentals within 20 miles that match your search

Vacation home in Hancock

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $2,863 / night

$34,302 / week

1 / 4

Great rentals within 20 miles that match your search

Vacation condo rental

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $430 / night

$3,006 / week

1 / 16

Great rentals within 20 miles that match your search

Stockbridge Vacation home rental

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $802 / night

$2,806 - $4,729 / week

1 / 19

Great rentals within 20 miles that match your search

Ski home to rent in Plainfield

Plainfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from $234 / night

$1,575 - $2,636 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation log cabin rental

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

from $487 / night

$1,890 - $2,090 / week

1 / 18

Great rentals within 20 miles that match your search

Lanesborough Vacation home rental

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

from $795 / night

$4,574 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation home in Great Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $572 / night

$4,000 / week

1 / 52

Great rentals within 20 miles that match your search

Vacation condo with shared pool in South Lee

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $81 / night

$561 / week

1 / 15

Great rentals within 20 miles that match your search

Vacation condo with shared pool in South Lee

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $70 / night

$489 / week

1 / 15