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> North America
> United States
> Massachusetts
> Berkshires

Best Berkshires Apartments on Holiday Lettings - Vacation rentals

Price per day

$1 $750 -

Bedrooms

Property rating (out of 5)
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  • 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

Why am I receiving these results?

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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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

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $682 / night

$3,779 / week

1 / 23

Home rental in Berkshires

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $172 / night

$1,203 / week

1 / 17

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 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

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 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 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

Ski apartment to rent in Great Barrington

Great Barrington apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Housekeeping Included

from $175 / night

$1,225 / week

1 / 14

Ski home to rent in New Marlborough

New Marlborough house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Housekeeping Included

from $1,600 / night

$11,200 / week

1 / 30

Monterey ski chalet to rent.

Monterey chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Housekeeping Included

from $200 / night

$1,400 / week

1 / 30

Berkshires ski home to rent.

Becket house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $217 / night

$1,519 / week

1 / 19

Ski home to rent in Berkshires

Hancock house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $225 / night

$1,575 / week

1 / 28

Berkshires ski home to rent.

New Ashford house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $223 / night

$1,561 / week

1 / 30

Ski home to rent in Berkshires

Pittsfield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $270 / night

$1,890 / week

1 / 30

Ski home to rent in West Stockbridge

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $325 / night

$2,275 / week

1 / 23

Vacation condo in Hancock

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $507 / night

$3,549 / week

1 / 30

Vacation home in Berkshires

Hancock house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $250 / night

$1,750 / week

1 / 20

Vacation condo in Lenox

Lenox condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $250 / night

$1,750 / week

1 / 17

Condo rental in Hancock

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 8

1 filter does not match: Housekeeping Included

from $381 / night

$2,667 / week

1 / 30

Berkshires Vacation cottage accommodation

Lenox cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Housekeeping Included

from $385 / night

$2,695 / week

1 / 8

Vacation cottage rental

Lenox cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $540 / night

$3,780 / week

1 / 7

Berkshires Vacation cottage rental

Lenox cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $465 / night

$3,255 / week

1 / 7

Condo accommodation in Berkshires

Pittsfield condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $654 / night

$4,578 / week

1 / 28

Ski home to rent in Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $479 / night

$3,353 / week

1 / 30

Ski home to rent in Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $225 / night

$1,575 / week

1 / 30

Berkshires Vacation home rental

Pittsfield house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $385 / night

$2,695 / week

1 / 13

Hancock ski studio to rent.

Hancock studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $168 / night

$1,176 / week

1 / 30

Ski condo to rent in Pittsfield

Pittsfield condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $499 / night

$3,493 / week

1 / 24

Ski home to rent in Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $413 / night

$2,891 / week

1 / 30

Vacation home in Hancock

Hancock house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $130 / night

$910 / week

1 / 16

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