We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Shelter Island, NY and nearby

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 45 Rentals in the Shelter Island Area
loading...
From
$179
Per Night
Shelter Island
4 Bedrooms, 4 Bathrooms, Sleeps 10
16 photos Details
Make Inquiry
From
$375
Per Night
Shelter Island
4 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
15 photos Details
Make Inquiry
From
$150
Per Night
Shelter Island
2 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
Reviews (3) Make Inquiry
From
$400
Per Night
Shelter Island
4 Bedrooms, 4 Bathrooms, Sleeps 10
30 photos Details
Make Inquiry
From
$325
Per Night
Shelter Island
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Make Inquiry
From
$357
Per Night
Shelter Island
3 Bedrooms, 3 Bathrooms, Sleeps 5
35 photos Details
Make Inquiry
From
$457
Per Night
Shelter Island
3 Bedrooms, 2 Bathrooms, Sleeps 5
4 photos Details
Make Inquiry
From
$1,100
Per Night
Shelter Island
6 Bedrooms, 8 Bathrooms, Sleeps 12
28 photos Details
Make Inquiry
From
$299
Per Night
Shelter Island
3 Bedrooms, 2 Bathrooms, Sleeps 4
7 photos Details
Make Inquiry
From
$750
Per Night
Shelter Island
5 Bedrooms, 4 Bathrooms, Sleeps 9
16 photos Details
Reviews (3) Make Inquiry
Get the List

The following rentals are within 5 miles of Shelter Island, Long Island, New York.

From
$275
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details
Make Inquiry
From
$295
Per Night
Southold, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
17 photos Details
Reviews (11) Make Inquiry
From
$175
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
13 photos Details
Reviews (1) Make Inquiry
From
$275
Per Night
Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Make Inquiry
From
$172
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (8) Make Inquiry
From
$300
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
15 photos Details
Make Inquiry
From
$175
Per Night
Orient, NY
Studio, 1 Bathroom, Sleeps 3
Bookings
23 photos Details
Reviews (10) Make Inquiry
From
$143
Per Night
Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 5
7 photos Details
Make Inquiry
From
$300
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
40 photos Details
Make Inquiry
From
$210
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
7 photos Details
Make Inquiry
From
$369
Per Night
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Reviews (20) Make Inquiry
From
$309
Per Night
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Reviews (24) Make Inquiry
From
$200
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 7
12 photos Details
Make Inquiry
From
$250
Per Night
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
14 photos Details
Reviews (1) Make Inquiry
From
$250
Per Night
Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 7
18 photos Details
Make Inquiry
From
$200
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Make Inquiry
From
$2,143
Per Night
East Marion, NY
6 Bedrooms, 5 Bathrooms, Sleeps 12
17 photos Details
Make Inquiry
From
$357
Per Night
Orient, NY
4 Bedrooms, 4 Bathrooms, Sleeps 8
23 photos Details
Make Inquiry
From
$260
Per Night
Orient, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Make Inquiry
From
$350
Per Night
Orient, NY
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
11 photos Details
Reviews (1) Make Inquiry
From
$250
Per Night
Greenport, NY
4 Bedrooms, 2 Bathrooms, Sleeps 10
23 photos Details
Reviews (2) Make Inquiry
From
$195
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
12 photos Details
Make Inquiry
From
$245
Per Night
Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
22 photos Details
Reviews (1) Make Inquiry
From
$250
Per Night
Southold, NY
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (2) Make Inquiry
From
$499
Per Night
Southold, NY
3 Bedrooms, 3 Bathrooms, Sleeps 8
8 photos Details
Make Inquiry
From
$171
Per Night
East Marion, NY
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Make Inquiry
From
$295
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
11 photos Details
Make Inquiry
From
$2,400
Per Week
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (2) Make Inquiry
From
$500
Per Night
Southold, NY
4 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (2) Make Inquiry
From
$200
Per Night
East Marion, NY
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
14 photos Details
Reviews (1) Make Inquiry
From
$314
Per Night
Orient, NY
2 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
Make Inquiry
From
$175
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
Make Inquiry
From
$295
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Make Inquiry
From
$321
Per Night
Southold, NY
4 Bedrooms, 4 Bathrooms, Sleeps 10
5 photos Details
Make Inquiry
Inquire for rates
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
3 photos Details
Make Inquiry
Go to map view
Book Online(22)
Use filters to find the best results!

Suitability

  • Wheelchair access (4)
  • Elder access (17)
  • Suitable for children (24)
  • Pet friendly (14)
  • Smoking allowed (2)

Amenities

  • Other outdoor space (38)
  • Air Conditioning (37)
  • Internet (37)
  • Grill (34)
  • Parking (31)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities
Filter search results by:
Book Online(22)

Suitability

  • Wheelchair access (4)
  • Elder access (17)
  • Suitable for children (24)
  • Pet friendly (14)
  • Smoking allowed (2)

Amenities

  • Other outdoor space (38)
  • Air Conditioning (37)
  • Internet (37)
  • Grill (34)
  • Parking (31)
  • View all amenities