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Best Berkshires Apartments on Holiday Lettings - Vacation rentals

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5 Vacation rentals

Great rentals within 20 miles that match your search

Vacation home in Clintondale

Clintondale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $859 / night

$6,012 / week

1 / 50

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

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

Home rental in Shaftsbury

Shaftsbury house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from $401 / night

$1,718 / week

1 / 11

Great rentals within 20 miles that match your search

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Apartment rental in Stafford Springs

Stafford Springs apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

1 filter does not match: Staffed property

from $172 / night

$1,203 / week

1 / 9

Great rentals within 20 miles that match your search

Springfield Vacation home rental

Springfield house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Housekeeping Included

from $147 / night

$1,026 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home in Haines Falls

Haines Falls house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 25

1 filter does not match: Staffed property

from $1,145 / night

$4,580 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation home in Plattekill

Plattekill house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $327 / night

$2,061 - $2,783 / week

1 / 11

Great rentals within 20 miles that match your search

Tented camp rental in Woodstock

Woodstock tented camp

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $263 / night

$1,836 / week

1 / 4

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: Staffed property

from $144 / night

$1,002 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation home in New Paltz

New Paltz house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Staffed property

from $75 / night

$481 / week

1 / 10

Great rentals within 20 miles that match your search

Vacation home in Saratoga Springs

Saratoga Springs house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Staffed property

from $353 / night

$2,175 - $2,976 / week

1 / 14

Great rentals within 20 miles that match your search

Roxbury Vacation hotel apartment rental

Roxbury hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $286 / night

$1,711 / week

1 / 7

Great rentals within 20 miles that match your search

Vacation cottage in Saratoga Springs

Saratoga Springs cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Housekeeping Included

from $172 / night

$1,031 - $1,832 / week

1 / 10

Great rentals within 20 miles that match your search

Vacation condo in Hancock

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $258 / night

$1,804 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation home in Millerton

Millerton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Housekeeping Included

from $287 / night

$1,603 - $7,615 / week

1 / 12

Great rentals within 20 miles that match your search

Vacation apartment rental

Palenville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Housekeeping Included

from $247 / night

$1,603 / week

1 / 22

Great rentals within 20 miles that match your search

Bondville Vacation home rental

Bondville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Staffed property

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

1 filter does not match: Staffed property

from $161 / night

$1,123 / week

1 / 20

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: Staffed property

from $160 / night

$1,114 / week

1 / 11

Great rentals within 20 miles that match your search

Apartment rental in Saratoga Springs

Saratoga Springs apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 filter does not match: Staffed property

from $1,025 / night

$6,298 / week

1 / 7

Great rentals within 20 miles that match your search

Vacation home in Hudson

Hudson house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Staffed property

from $1,145 / night

$6,870 - $9,275 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation barn with golf nearby in Manchester

Manchester barn

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Housekeeping Included

from $458 / night

$3,206 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation manor house in Marlborough

Marlborough manor house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 22

1 filter does not match: Housekeeping Included

from $4,122 / night

$28,854 / week

1 / 52

Great rentals within 20 miles that match your search

Ski home to rent in Peru

Peru house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Staffed property

from $401 / night

$2,519 - $2,920 / week

1 / 43

Great rentals within 20 miles that match your search

Brimfield Vacation home rental

Brimfield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: Staffed property

from $1,031 / night

$7,214 / week

1 / 24

Great rentals within 20 miles that match your search

Ski condo to rent in Berkshires

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 filter does not match: Staffed property

from $260 / night

$1,489 / week

1 / 39

Great rentals within 20 miles that match your search

Vacation cottage in Hinsdale

Hinsdale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Staffed property

from $287 / night

$1,718 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Maplecrest

Maplecrest house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Staffed property

from $487 / night

$3,149 / week

1 / 50

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: Staffed property

from $1,374 / night

$9,618 / week

1 / 38

Great rentals within 20 miles that match your search

Vacation tower in Granville

Granville tower

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Staffed property

from $344 / night

$2,061 / week

1 / 16

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: Staffed property

from $172 / night

$573 / week

1 / 9

Great rentals within 20 miles that match your search

Vacation apartment in New Paltz

New Paltz apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Staffed property

from $413 / night

$2,748 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home in Kingston

Kingston house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Staffed property

from $458 / night

$2,405 / week

1 / 39

Great rentals within 20 miles that match your search

Vacation apartment accommodation

Dover apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Staffed property

from $401 / night

$1,145 / week

1 / 17

Great rentals within 20 miles that match your search

Lodge rental in Lake Luzerne

Lake Luzerne lodge

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Staffed property

from $858 / night

$6,004 / week

1 / 19

Great rentals within 20 miles that match your search

Home rental in Rhinebeck

Rhinebeck house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Staffed property

from $298 / night

$2,061 / week

1 / 27

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

1 filter does not match: Staffed property

from $269 / night

$1,884 / week

1 / 36

Great rentals within 20 miles that match your search

Bondville ski villa to rent.

Bondville villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Staffed property

from $1,123 / night

$7,855 / week

1 / 55

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