Shelter Island Vacation Rentals

Compare 868 available properties from 17 providers
Shelter Island

Discover a rental matching your expectations among the 868 welcoming rentals from numerous vacation rental websites in Shelter Island. HomeToGo directly shows the best offers by comparing all of the listed properties in Shelter Island from its various partners.

Recommended Vacation Rentals on Shelter Island

Rent a vacation accommodation on Shelter Island: from $111 per night

House ∙ 4 guests ∙ 2 bedrooms
Greenport, Southold, New York, United States
from $117
VRBO
4.0
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Apartment ∙ 4 guests ∙ 4 bedrooms
Greenport, Southold, New York, United States
from $117
VRBO
4.5
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House ∙ 5 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $601
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $415
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $394
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $263
VRBO
5.0
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House ∙ 8 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
from $533
VRBO
5.0
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House ∙ 8 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $793
VRBO
5.0
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House ∙ 9 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
from $426
VRBO
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 2 bedrooms
Shelter Island, Suffolk County, New York, United States
from $192
VRBO
4.9
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Fishing
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $254
VRBO
4.9
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Fishing
House ∙ 4 guests ∙ 2 bedrooms
Shelter Island, Suffolk County, New York, United States
from $368
VRBO
5.0
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $340
VRBO
5.0
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $246
VRBO
4.8
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $930
VRBO
5.0
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Vacation Houses With Pools

Pool
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $382
VRBO
4.6
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Pool
House ∙ 7 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
from $218
VRBO
5.0
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Pool
House ∙ 8 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
from $643
VRBO
5.0
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Popular Rental Amenities on Shelter Island

  • Kitchen (562)
  • No smoking (543)
  • Internet (542)
  • AC (523)
  • Parking (497)
  • TV (488)
  • Washer (456)
  • Grill (433)
  • Microwave (402)
  • Dishwasher (396)
  • Yard (361)
  • Fireplace (336)
Our search page's filters will help you find the perfect rental in Shelter Island. You can easily search and find a rental matching your expectations in Shelter Island if you need internet access during your vacation or you want to tune out with some TV time, as most accommodations provide "internet" or "TVs." You can also search for a property on Shelter Island if you travel with your pet as 188 of the listed rentals there provide "Pets Allowed."

Price and Availability Index in Shelter Island

Vacation Rental Price Information on Shelter Island

The price graph will give you the nightly price average for the upcoming months of the year. Prices reach a peak a week in July. The price per night in a vacation rental on Shelter Island this week (7/27 - 8/3) costs on average $749. Prices drop in March to an average of $649 per night (3/30 - 4/6).

Rental Availability Information on Shelter Island

Check how busy Shelter Island is with our availability graph. So far, the week with the least available rentals on Shelter Island is in November (11/2 - 11/9). On the contrary, only 14% of the rentals are booked during a week in January (1/5 - 1/12).

The Weather on Shelter Island

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30°
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30°
45°
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55°
45°
64°
54°
73°
61°
79°
68°
77°
66°
72°
61°
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54°
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43°
46°
37°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Shelter Island climate diagram. The highest average temperatures are in the month of July. No heat wave is expected in January, where minimum average temperatures usally hit a 30° low. The rainiest month is July while the driest month is August.

Accommodations on Shelter Island

In Shelter Island, most of the 868 accommodation types are house rentals, which represent 82.08% of its available accommodations. Interestingly, the average rental fee for this type of accommodation in particular is $1,070 a night, with an average size of 2,480 ft². Furthermore, these accommodations are perfect for large groups, as most can accommodate 8 people. If you would prefer to book another accommodation type, you may want to check hotel rooms, which are the second most typical type of accommodation in Shelter Island. Our data reveals that the average price of hotel rooms is $358 per night for an area of 580 ft².

Experience heaven on earth with Shelter Island vacation rentals

Shelter Island is merely 90 miles west of Manhattan, but offers a tranquil escape from the humdrum of city life. Reach the 8,000-acre island sandwiched between North and South Forks of Long Island by ferry, to explore the 17 miles of unspoiled coastline.

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Family Activities

Spend time outdoors with kids

With 12 miles of coastline and 2,000 acres of woodlands, marshes, and creeks, Mashomack Preserve covers the entire south-eastern part of Shelter Island.

A nearby vacation cabin ensures quick access to the Field House to explore the interactive exhibit about the Preserve’s ecosystem. Choose from five hiking trails of varying lengths and spot ospreys, piping plovers, and least terns.

Local Attractions

Relax and unwind by the sea

Rent a beach house on the secluded and tranquil Shell Beach. This narrow beach extends into the Shelter Island Sound. Bask in the sun, watch plovers hop close to the waters edge, and be mesmerized by the colorful wildflowers in the vicinity, and the panoramic views of the South Fork and West Neck Harbor.

We compare more than 300 providers, including:

Booking.com Vacation Rentals on Shelter Island VRBO Vacation Rentals on Shelter Island HomeAway Vacation Rentals on Shelter Island TripAdvisor Vacation Rentals on Shelter Island VacationRentals.com Vacation Rentals on Shelter Island HouseTrip Vacation Rentals on Shelter Island FlipKey Vacation Rentals on Shelter Island Wimdu Vacation Rentals on Shelter Island 9flats.com Vacation Rentals on Shelter Island VaycayHero Vacation Rentals on Shelter Island PerfectPlaces.com Vacation Rentals on Shelter Island Homestay.com Vacation Rentals on Shelter Island Only-apartments Vacation Rentals on Shelter Island Interhome Vacation Rentals on Shelter Island Bedycasa Vacation Rentals on Shelter Island Novasol Vacation Rentals on Shelter Island HomeEscape Vacation Rentals on Shelter Island

Vacation Destinations Near Shelter Island