Viewing 40 of 3,397 rentals in Shelter Island
Tell us your dates, and we will find the most accurate rates and availability for you
Updating
Best Shelter Island Apartments on Holiday Lettings - Vacation rentals
113 Vacation rentals
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $325 / night
$2,275 / week
from $315 / night
$2,205 / week
Shelter Island Heights ski cottage to rent.
Shelter Island Heights cottage
- 3 bedrooms
- 1 bathroom
- sleeps 4
from $334 / night
$2,338 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
from $450 / night
$3,150 / week
Ski home to rent in Shelter Island Heights
Shelter Island Heights house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
from $580 / night
$4,060 / week
Shelter Island Heights ski home to rent.
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
from $506 / night
$3,542 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
from $646 / night
$4,522 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $618 / night
$4,326 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $368 / night
$2,576 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
from $775 / night
$5,425 / week
Shelter Island Heights ski home to rent.
Shelter Island Heights house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
from $991 / night
$6,937 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $593 / night
$4,151 / week
from $573 / night
$4,011 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $651 / night
$4,557 / week
Ski home to rent in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $644 / night
$4,508 / week
Ski home to rent in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $599 / night
$4,193 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $538 / night
$3,766 / week
from $328 / night
$2,296 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 4 bedrooms
- 4 bathrooms
- sleeps 5
from $431 / night
$3,017 / week
Vacation apartment in Shelter Island Heights
Shelter Island Heights apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
from $325 / night
$2,275 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
from $671 / night
$4,697 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 5
from $769 / night
$5,383 / week
from $593 / night
$4,151 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 5 bedrooms
- 2 bathrooms
- sleeps 8
from $381 / night
$2,667 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
from $967 / night
$6,769 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
from $469 / night
$3,283 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $891 / night
$6,237 / week
Ski home to rent in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
from $558 / night
$3,906 / week
Ski home to rent in Shelter Island Heights
Shelter Island Heights house
- 5 bedrooms
- 4 bathrooms
- sleeps 10
from $786 / night
$5,502 / week
from $610 / night
$4,270 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $550 / night
$3,850 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $620 / night
$4,340 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
from $738 / night
$5,166 / week
Ski home to rent in Shelter Island Heights
Shelter Island Heights house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $571 / night
$3,997 / week
from $383 / night
$2,681 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 2 bedrooms
- 1 bathroom
- sleeps 4
from $494 / night
$3,458 / week
from $870 / night
$6,090 / week
Shelter Island Heights Vacation home rental
Shelter Island Heights house
- 6 bedrooms
- 3 bathrooms
- sleeps 12
from $790 / night
$5,530 / week
Shelter Island Heights ski home to rent.
Shelter Island Heights house
- 7 bedrooms
- 5 bathrooms
- sleeps 15
from $1,242 / night
$8,694 / week
Vacation home in Shelter Island Heights
Shelter Island Heights house
- 4 bedrooms
- 3 bathrooms
- sleeps 6
from $1,016 / night
$7,112 / week