Updating

50 Best Berkshires Apartments on Holiday Lettings - Vacation rentals

All filters

Filters

90 Vacation rentals

Monterey Vacation cottage rental

Monterey cottage

1 bedroom • 1 bathroom • sleeps 4

1 review

from $174 / night

$1,219 / week

1 / 25

Berkshires Vacation cottage rental

Monterey cottage

2 bedrooms • 1 bathroom • sleeps 2

4 reviews

from $324 / night

$2,269 / week

1 / 24

Home rental in Berkshires

Becket house

4 bedrooms • 3 bathrooms • sleeps 8

4 reviews

from $315 / night

$1,374 / week

1 / 20

Vacation home in Hinsdale

Hinsdale house

3 bedrooms • 2 bathrooms • sleeps 6

from $218 / night

$1,168 - $1,374 / week

1 / 10

Vacation home in Monterey

Monterey house

4 bedrooms • 5 bathrooms • sleeps 10

from $516 / night

$3,607 / week

1 / 23

Vacation home in Becket

Becket house

2 bedrooms • 1 bathroom • sleeps 4

13 reviews

from $171 / night

$1,140 / week

1 / 13

Vacation condo in Hancock

Hancock condo

1 bedroom • 2 bathrooms • sleeps 4

from $258 / night

$1,804 / week

1 / 14

Vacation apartment in Charlemont

Charlemont apartment

1 bedroom • 1 bathroom • sleeps 4

180 reviews

from $172 / night

$1,088 - $1,569 / week

1 / 37

Berkshires Vacation home rental

Monterey house

5 bedrooms • 2 bathrooms • sleeps 6

from $573 / night

$4,008 / week

1 / 3

Vacation apartment in Berkshires

Lenox apartment

4 bedrooms • 1 bathroom • sleeps 7

35 reviews

from $229 / night

$1,374 / week

1 / 21

Vacation home rental

Great Barrington house

4 bedrooms • 2 bathrooms • sleeps 10

4 reviews

from $251 / night

$1,260 - $2,691 / week

1 / 18

Vacation home with golf nearby in Berkshires

Lee house

5 bedrooms • 6 bathrooms • sleeps 9

5 reviews

from $818 / night

$5,725 / week

1 / 18

Vacation cottage rental

Great Barrington cottage

1 bedroom • 1 bathroom • sleeps 3

24 reviews

from $263 / night

$1,483 - $2,176 / week

1 / 18

Vacation apartment in Berkshires

Lee apartment

3 bedrooms • 2 bathrooms • sleeps 8

2 reviews

from $373 / night

$2,605 - $3,407 / week

1 / 12

Vacation home in Lenox

Lenox house

3 bedrooms • 3 bathrooms • sleeps 6

from $252 / night

$1,764 / week

1 / 24

Vacation home in Berkshires

Hancock house

4 bedrooms • 2 bathrooms • sleeps 8

1 review

from $144 / night

$902 - $2,304 / week

1 / 26

Vacation home in Berkshires

Otis house

6 bedrooms • 5 bathrooms • sleeps 14

from $687 / night

$4,809 - $6,412 / week

1 / 22

Berkshires Vacation home rental

Savoy house

2 bedrooms • 1 bathroom • sleeps 4

9 reviews

from $229 / night

$1,374 / week

1 / 6

Vacation home in Berkshires

Great Barrington house

5 bedrooms • 4 bathrooms • sleeps 12

4 reviews

from $344 / night

$3,035 - $3,996 / week

1 / 30

Berkshires Vacation home rental

Monterey house

• 2 bathrooms • sleeps 7

from $205 / night

$1,432 / week

1 / 12

Apartment rental in Lee with shared pool

Lee apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $430 / night

$2,863 / week

1 / 12

Vacation home in Lenox

Lenox house

2 bedrooms • 2 bathrooms • sleeps 4

2 reviews

from $229 / night

$1,603 / week

1 / 12

Vacation home rental

West Stockbridge house

5 bedrooms • 2 bathrooms • sleeps 15

42 reviews

from $298 / night

$1,775 - $3,579 / week

1 / 20

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

Stockbridge house

3 bedrooms • 2 bathrooms • sleeps 6

from $859 / night

$5,153 / week

1 / 22

Vacation home rental

Stockbridge house

3 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $427 / night

$2,990 / week

1 / 30

Cottage accommodation in Berkshires

Stockbridge cottage

3 bedrooms • 2 bathrooms • sleeps 7

6 reviews

from $327 / night

$2,290 / week

1 / 16

Berkshires Vacation condo rental

Williamstown condo

2 bedrooms • 1 bathroom • sleeps 4

from $262 / night

$1,832 / week

1 / 6

Vacation farmhouse in Berkshires

Stockbridge farmhouse

1 bedroom • 1 bathroom • sleeps 3

from $172 / night

$1,031 / week

1 / 4

Vacation home in Berkshires

Lee house

5 bedrooms • 5 bathrooms • sleeps 12

from $859 / night

$3,435 / week

1 / 7

Vacation log cabin rental

East Otis log cabin

2 bedrooms • 1 bathroom • sleeps 4

from $121 / night

$842 / week

1 / 24

Vacation home in Berkshires

Becket house

3 bedrooms • 3 bathrooms • sleeps 8

from $385 / night

$2,693 / week

1 / 42

Great Barrington Vacation home rental

Great Barrington house

3 bedrooms • 2 bathrooms • sleeps 4

1 review

from $172 / night

$1,088 / week

1 / 14

Vacation home in Berkshires

Hancock house

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from $2,863 / night

$34,302 / week

1 / 4

Vacation farmhouse in Berkshires

Stockbridge farmhouse

1 bedroom • 1 bathroom • sleeps 2

from $172 / night

$1,031 / week

1 / 4

Vacation home in Lenox

Lenox house

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from $251 / night

$1,756 / week

1 / 24

Vacation condo with shared pool in Berkshires

Hancock condo

2 bedrooms • 2 bathrooms • sleeps 8

from $229 / night

$1,603 / week

1 / 8

Vacation studio in Berkshires

Hancock studio

Studio • 1 bathroom • sleeps 4

from $124 / night

$869 - $3,360 / week

1 / 67

Vacation b&b in West Stockbridge

West Stockbridge b&b

2 bedrooms • 2 bathrooms • sleeps 4

from $241 / night

$1,684 / week

1 / 16

Vacation home in Berkshires

Lenox house

2 bedrooms • 2 bathrooms • sleeps 4

from $515 / night

$3,599 / week

1 / 25

×

Also consider