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Best Pittsfield Apartments on Holiday Lettings - Apartment rentals

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15 Vacation rentals

Great rentals within 20 miles that match your search

Vacation home in Hancock

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $172 / night

$902 - $2,304 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation apartment in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

from $229 / night

$1,374 / week

1 / 21

Great rentals within 20 miles that match your search

Home rental in Lenox

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $172 / night

$1,203 / week

1 / 17

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 studio in Hancock

Hancock studio

  • Studio
  • 1 bathroom
  • sleeps 4

from $111 / night

$777 - $2,130 / week

1 / 67

Great rentals within 20 miles that match your search

Vacation home in Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $344 / night

$2,405 / week

1 / 12

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

Williamstown Vacation condo rental

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $262 / night

$1,832 / week

1 / 6

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

Vacation home in Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $343 / night

$2,397 / week

1 / 25

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