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Best Berkshires Apartments on Holiday Lettings - Vacation rentals

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3 Vacation rentals

Great rentals within 20 miles that match your search

Home rental in Manhasset

Manhasset house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $670 / night

$4,689 / week

1 / 21

Great rentals within 20 miles that match your search

Southampton Vacation home rental

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

from $5,153 / night

$36,068 / week

1 / 83

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,374 / night

$9,618 / week

1 / 20

Great rentals within 20 miles that match your search

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Wallingford Vacation b&b rental

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private outdoor pool (heated)

from $224 / night

$1,563 / week

1 / 4

Great rentals within 20 miles that match your search

Wallingford Vacation b&b rental

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private outdoor pool (heated)

from $224 / night

$1,563 / week

1 / 4

Great rentals within 20 miles that match your search

Wallingford Vacation b&b rental

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private outdoor pool (heated)

from $224 / night

$1,563 / week

1 / 4

Great rentals within 20 miles that match your search

Wallingford Vacation b&b rental

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private outdoor pool (heated)

from $224 / night

$1,563 / week

1 / 4

Great rentals within 20 miles that match your search

Sag Harbor Vacation home rental

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $1,276 / night

$8,931 / week

1 / 7

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $1,918 / night

$13,426 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home in Suffern

Suffern house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $573 / night

$1,947 / week

1 / 32

Great rentals within 20 miles that match your search

Vacation home in Water Mill

Water Mill house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

1 filter does not match: Housekeeping Included

from $630 / night

$4,409 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation home in Westhampton Beach

Westhampton Beach house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 16

1 filter does not match: Housekeeping Included

from $1,432 / night

$4,008 - $14,313 / week

1 / 30

Great rentals within 20 miles that match your search

Vacation home in Noyack

Noyack house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $1,718 / night

$12,023 / week

1 / 42

Great rentals within 20 miles that match your search

Vacation villa rental

White Plains villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 filter does not match: Housekeeping Included

from $458 / night

$2,863 / week

1 / 108

Great rentals within 20 miles that match your search

Vacation home rental

Accord house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $916 / night

$5,611 - $7,786 / week

1 / 14

Great rentals within 20 miles that match your search

Monroe Vacation apartment rental

Monroe apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 filter does not match: Housekeeping Included

from $401 / night

$2,290 / week

1 / 10

Great rentals within 20 miles that match your search

Home rental in Southold

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Housekeeping Included

from $430 / night

$2,205 / week

1 / 21

Great rentals within 20 miles that match your search

Greenport Vacation home rental

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $916 / night

$6,412 / week

1 / 22

Great rentals within 20 miles that match your search

Bridgehampton Vacation home accommodation

Bridgehampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $1,718 / night

$16,603 / week

1 / 18

Great rentals within 20 miles that match your search

Queensbury Vacation home rental

Queensbury house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

1 filter does not match: Housekeeping Included

from $859 / night

$6,012 / week

1 / 37

Great rentals within 20 miles that match your search

Apartment rental in Stafford Springs

Stafford Springs apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

1 filter does not match: Private outdoor pool (heated)

from $172 / night

$1,203 / week

1 / 9

Great rentals within 20 miles that match your search

Vacation cottage rental

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

1 filter does not match: Housekeeping Included

from $3,272 / night

$22,900 / week

1 / 15

Great rentals within 20 miles that match your search

Amagansett Vacation home rental

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $1,309 / night

$9,160 / week

1 / 11

Great rentals within 20 miles that match your search

Vacation home with indoor pool in Amagansett

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $1,088 / night

$4,008 / week

1 / 6

Great rentals within 20 miles that match your search

East Quogue Vacation home rental

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $2,061 / night

$14,427 / week

1 / 30

Great rentals within 20 miles that match your search

Vacation home with swimming pool in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $343 / night

$2,397 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Housekeeping Included

from $1,064 / night

$7,443 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation b&b in Broadalbin

Broadalbin b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Housekeeping Included

from $126 / night

$687 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation home in Remsenburg

Remsenburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $258 / night

$3,607 / week

1 / 20

Great rentals within 20 miles that match your search

Amagansett Vacation home rental

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Housekeeping Included

from $1,603 / night

$11,221 / week

1 / 15

Great rentals within 20 miles that match your search

Vacation home rental

Remsenburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Housekeeping Included

from $572 / night

$4,000 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation home rental

Mastic house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

1 filter does not match: Housekeeping Included

from $859 / night

$6,012 / week

1 / 59

Great rentals within 20 miles that match your search

Vacation home in Southold

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 filter does not match: Housekeeping Included

from $2,469 / night

$5,043 - $10,407 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Aquebogue

Aquebogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Housekeeping Included

from $372 / night

$2,312 - $6,267 / week

1 / 34

Great rentals within 20 miles that match your search

Vacation home in Killington

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $244 / night

$1,708 / week

1 / 54

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: Private outdoor pool (heated)

from $1,145 / night

$4,580 / week

1 / 19

Great rentals within 20 miles that match your search

Private room rental in Teterboro

Teterboro private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private outdoor pool (heated)

from $75 / night

$521 / week

1 / 12

Great rentals within 20 miles that match your search

Vacation home with golf nearby in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Housekeeping Included

from $2,519 / night

$14,313 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation villa in Southampton

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Housekeeping Included

from $2,290 / night

$13,740 / week

1 / 11

Great rentals within 20 miles that match your search

Vacation home in Westhampton

Westhampton house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

1 filter does not match: Housekeeping Included

from $1,145 / night

$8,015 / week

1 / 13

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