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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)
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  • 4 and above
  • 3 and above
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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
  • Apartment (1)
  • Villa (2)
  • Cottage (1)
  • House (8)
  • Lodge (1)
  • Manor House (1)
  • Tower (1)
  • B&B (2)

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17 Vacation rentals

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Great rentals within 20 miles that match your search

Vacation apartment accommodation

Dover apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8
6 reviews

from $401 / night

$1,145 / week

1 / 17

Great rentals within 20 miles that match your search

Bondville Vacation home rental

Bondville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from $413 / night

$1,477 / week

1 / 15

Great rentals within 20 miles that match your search

New Paltz Vacation b&b rental

New Paltz b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $161 / night

$1,123 / week

1 / 20

Great rentals within 20 miles that match your search

Lodge rental in Lake Luzerne

Lake Luzerne lodge

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 12

from $858 / night

$6,004 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation home in Hudson

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,145 / night

$6,870 - $9,275 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation tower in Granville

Granville tower

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $344 / night

$2,061 / week

1 / 16

Great rentals within 20 miles that match your search

Ski villa to rent in South Newfane

South Newfane villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

from $1,718 / night

$12,023 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation b&b in Highland

Highland b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $252 / night

$1,764 / week

1 / 45

Great rentals within 20 miles that match your search

Ski manor house to rent in Middletown

Middletown manor house

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 12

from $1,002 / night

$5,725 / week

1 / 9

Great rentals within 20 miles that match your search

Home rental in Highland with swimming pool, golf nearby

Highland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6
2 reviews

from $269 / night

$1,884 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Maplecrest

Maplecrest house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from $487 / night

$3,149 / week

1 / 50

Great rentals within 20 miles that match your search

Vacation home in Stone Ridge

Stone Ridge house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $572 / night

$4,008 / week

1 / 41

Great rentals within 20 miles that match your search

Vacation home in Kingston

Kingston house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $458 / night

$2,405 / week

1 / 39

Great rentals within 20 miles that match your search

Bondville ski villa to rent.

Bondville villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $1,123 / night

$7,855 / week

1 / 55

Great rentals within 20 miles that match your search

Vacation cottage in Hinsdale

Hinsdale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $287 / night

$1,718 / week

1 / 29

Great rentals within 20 miles that match your search

Ski home to rent in Peru

Peru house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from $401 / night

$2,519 - $2,920 / week

1 / 43

Great rentals within 20 miles that match your search

Wilton Vacation home rental

Wilton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

from $573 / night

$4,008 - $17,404 / week

1 / 114

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Vacation home in Saugerties

Saugerties house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $453 / night

$2,061 / week

1 / 10

Great rentals within 20 miles that match your search

Home rental in Danbury

Danbury house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $343 / night

$2,397 / week

1 / 40

Great rentals within 20 miles that match your search

Bondville ski condo to rent.

Bondville condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

1 filter does not match: Housekeeping Included

from $171 / night

$1,195 / week

1 / 15

Great rentals within 20 miles that match your search

Bondville ski home to rent.

Bondville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

1 filter does not match: Housekeeping Included

from $286 / night

$1,996 / week

1 / 32

Great rentals within 20 miles that match your search

Home rental in Nassau

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Housekeeping Included

from $298 / night

$2,004 - $2,645 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation guest house in Amherst

Amherst guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Ceiling Fans

from $160 / night

$1,114 / week

1 / 11

Great rentals within 20 miles that match your search

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

Great rentals within 20 miles that match your search

Old Chatham Vacation villa rental

Old Chatham villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 16

1 filter does not match: Ceiling Fans

from $1,260 / night

$8,359 / week

1 / 38

Great rentals within 20 miles that match your search

Shelburne Falls Vacation private room rental

Shelburne Falls private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Ceiling Fans

from $144 / night

$1,002 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation apartment rental

Albany apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Ceiling Fans

from $172 / night

$573 / week

1 / 9

Great rentals within 20 miles that match your search

Home rental in Saugerties

Saugerties house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Housekeeping Included

from $458 / night

$3,206 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation home in Athens

Athens house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Housekeeping Included

from $401 / night

$2,806 / week

1 / 21

Great rentals within 20 miles that match your search

Vacation home rental

Middle Grove house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Housekeeping Included

from $201 / night

$1,363 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation home in Lake Luzerne

Lake Luzerne house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Housekeeping Included

from $287 / night

$2,004 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Wallingford

Wallingford house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $264 / night

$1,718 / week

1 / 16

Great rentals within 20 miles that match your search

Vacation apartment in Troy

Troy apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $115 / night

$802 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home rental

Newbury house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 13

1 filter does not match: Housekeeping Included

from $430 / night

$3,006 / week

1 / 11

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

1 filter does not match: Housekeeping Included

2 reviews

from $109 / night

$630 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation home in Tannersville

Tannersville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $573 / night

$3,264 / week

1 / 16

Great rentals within 20 miles that match your search

Lodge rental in Grafton

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

1 filter does not match: Housekeeping Included

from $2,176 / night

$11,450 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation villa in Acra

Acra villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Housekeeping Included

from $344 / night

$2,405 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation home in Middlefield

Middlefield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $144 / night

$1,432 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation home in Middlefield

Middlefield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $573 / night

$3,035 / week

1 / 32

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