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> Massachusetts
> Berkshires

Best Berkshires Apartments on Holiday Lettings - Vacation rentals

Price per day

$1 $750 -

Bedrooms

Property rating (out of 5)
  • 5
  • 4 and above
  • 3 and above
Tripadvisor rating Vrbo rating
Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Condo (1)

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1 Vacation rentals

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Ski condo to rent in Berkshires

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $260 / night

$1,489 / week

1 / 39

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Vacation home rental

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Housekeeping Included

1 review

from $327 / night

$2,290 / week

1 / 20

Berkshires Vacation condo rental

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $262 / night

$1,832 / week

1 / 6

Vacation home with golf nearby in Berkshires

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

1 filter does not match: Housekeeping Included

6 reviews

from $818 / night

$5,725 / week

1 / 18

Vacation apartment in Berkshires

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

2 reviews

from $373 / night

$2,605 - $3,407 / week

1 / 12

Vacation home rental

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

1 filter does not match: Housekeeping Included

44 reviews

from $298 / night

$1,775 - $3,579 / week

1 / 20

Vacation condo rental

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

1 review

from $430 / night

$3,006 / week

1 / 16

Great Barrington Vacation home rental

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

1 review

from $172 / night

$1,088 / week

1 / 14

Vacation home in Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

1 review

from $2,863 / night

$34,302 / week

1 / 4

Vacation home in Becket

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

13 reviews

from $171 / night

$1,140 / week

1 / 13

Vacation apartment in Berkshires

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

1 filter does not match: Housekeeping Included

40 reviews

from $229 / night

$1,374 / week

1 / 21

Vacation home in Hinsdale

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $218 / night

$1,168 - $1,248 / week

1 / 10

Vacation home in Monterey

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

1 review

from $573 / night

$4,008 / week

1 / 23

Vacation apartment in East Otis

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

1 review

from $126 / night

$802 / week

1 / 20

Stockbridge Vacation home rental

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $802 / night

$2,806 - $4,729 / week

1 / 19

Lanesborough Vacation home rental

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 filter does not match: Housekeeping Included

3 reviews

from $795 / night

$4,574 / week

1 / 18

Vacation cottage rental

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Housekeeping Included

24 reviews

from $274 / night

$1,831 / week

1 / 18

Berkshires Vacation home rental

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

9 reviews

from $229 / night

$1,374 / week

1 / 6

Ski home to rent in Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $567 / night

$3,435 / week

1 / 28

Vacation home in Berkshires

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $744 / night

$5,202 / week

1 / 58

Vacation home with swimming pool in Lee

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $659 / night

$4,609 / week

1 / 91

Vacation home in Great Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $572 / night

$4,000 / week

1 / 52

Vacation home in Berkshires

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $458 / night

$3,206 / week

1 / 31

Sheffield Vacation home rental

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $686 / night

$4,801 / week

1 / 74

Vacation home in Berkshires

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

1 review

from $343 / night

$2,397 / week

1 / 25

Vacation condo with shared pool in Berkshires

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $70 / night

$489 / week

1 / 15

Vacation studio in Berkshires

Hancock studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $122 / night

$848 - $2,130 / week

1 / 67

Vacation home rental

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $263 / night

$1,661 - $2,806 / week

1 / 18

Vacation condo with shared pool in Berkshires

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $70 / night

$489 / week

1 / 15

Ski home to rent in Becket

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $137 / night

$959 / week

1 / 27

Ski home to rent in Berkshires

Lanesborough house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Housekeeping Included

from $150 / night

$1,050 / week

1 / 25

Home rental in Berkshires

Becket house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 filter does not match: Housekeeping Included

from $145 / night

$1,015 / week

1 / 17

Berkshires ski home to rent.

Sheffield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $283 / night

$1,981 / week

1 / 30

Ski home to rent in Berkshires

East Otis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $253 / night

$1,771 / week

1 / 27

Vacation chalet in Berkshires

Tyringham chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 filter does not match: Housekeeping Included

from $237 / night

$1,659 / week

1 / 30

Berkshires ski home to rent.

Charlemont house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Housekeeping Included

from $402 / night

$2,814 / week

1 / 30

Great Barrington ski home to rent.

Great Barrington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Housekeeping Included

from $425 / night

$2,975 / week

1 / 29

Home rental in Berkshires

Williamstown house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $690 / night

$4,830 / week

1 / 23

Berkshires ski home to rent.

Pittsfield house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: Housekeeping Included

from $500 / night

$3,500 / week

1 / 30

Berkshires ski home to rent.

Adams house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: Housekeeping Included

from $508 / night

$3,556 / week

1 / 30

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