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Best Vacation Rentals in Shelter Island Heights - Holiday Lettings - Cabins

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112 Vacation rentals

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Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $317 / night

$2,219 / week

1 / 26

Vacation home rental

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $315 / night

$2,205 / week

1 / 27

Shelter Island Heights ski cottage to rent.

Shelter Island Heights cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from $364 / night

$2,548 / week

1 / 18

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $450 / night

$3,150 / week

1 / 30

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $580 / night

$4,060 / week

1 / 23

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $506 / night

$3,542 / week

1 / 30

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $646 / night

$4,522 / week

1 / 24

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $618 / night

$4,326 / week

1 / 30

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $363 / night

$2,541 / week

1 / 21

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $775 / night

$5,425 / week

1 / 22

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $991 / night

$6,937 / week

1 / 22

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $593 / night

$4,151 / week

1 / 23

Home rental in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $573 / night

$4,011 / week

1 / 24

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $651 / night

$4,557 / week

1 / 13

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $644 / night

$4,508 / week

1 / 13

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $676 / night

$4,732 / week

1 / 24

Home rental in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

from $325 / night

$2,275 / week

1 / 24

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 5

from $438 / night

$3,066 / week

1 / 30

Vacation apartment in Shelter Island Heights

Shelter Island Heights apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $325 / night

$2,275 / week

1 / 16

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $741 / night

$5,187 / week

1 / 24

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $769 / night

$5,383 / week

1 / 23

Home rental in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $605 / night

$4,235 / week

1 / 27

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

from $377 / night

$2,639 / week

1 / 30

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $967 / night

$6,769 / week

1 / 23

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 8

from $558 / night

$3,906 / week

1 / 18

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $528 / night

$3,696 / week

1 / 30

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $891 / night

$6,237 / week

1 / 13

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $558 / night

$3,906 / week

1 / 21

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $786 / night

$5,502 / week

1 / 30

Home rental in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $567 / night

$3,969 / week

1 / 30

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $569 / night

$3,983 / week

1 / 18

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $620 / night

$4,340 / week

1 / 27

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $718 / night

$5,026 / week

1 / 21

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $571 / night

$3,997 / week

1 / 30

Vacation home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $379 / night

$2,653 / week

1 / 30

Shelter Island Heights Vacation home rental

Shelter Island Heights house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $491 / night

$3,437 / week

1 / 11

Vacation home rental

Shelter Island Heights house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $870 / night

$6,090 / week

1 / 22

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

from $730 / night

$5,110 / week

1 / 24

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

from $1,242 / night

$8,694 / week

1 / 20

Vacation home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,016 / night

$7,112 / week

1 / 28