Shelter Island Vacation Rentals

Our Favorite Vacation Rentals in Shelter Island

  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Remodeled Greenport Apartment By Greenport Harbor
     Home/Apartment
    HolidayLettings
    From
    $331
  • The Farm on the North Fork
     Country House
    Booking.com
    From
    $284
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,345
  • Kid’s Beach Haven
     Country House
    Booking.com
    From
    $1,600
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $643
  • Southampton Waterfront House
     Villa
    Booking.com
    From
    $1,060
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $573

Check prices for these upcoming dates

Shelter Island Vacation Rentals with a Pool

  • Chic Shelter Island Home, Pool and Gardens
    Excellent3br Home/Apartment
    Airbnb
    From
    $650
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $410
  • Modern, spacious SI home with heated gunite pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $706
  • Secluded and Sheltered
    Excellent4br Home/Apartment
    Airbnb
    From
    $336

Shelter Island Vacation Rentals with Wi-Fi

  • Three bedroom apartment
    Good3br Home/Apartment
    Airbnb
    From
    $252
  • Family Friendly Island Home
    Excellent4br Home/Apartment
    Airbnb
    From
    $509
  • Spacious Shelter Island home near bay & beach
    Excellent4br Home/Apartment
    Airbnb
    From
    $424
  • Two bedroom bungalow with sleeping loft
    Excellent2br Home/Apartment
    Airbnb
    From
    $390

Shelter Island Pet-Friendly Vacation Rentals

  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $419
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • East Hampton Classic
    Excellent4br Home/Apartment
    Flipkey
    From
    $1,487
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $2,605

Shelter Island Travel Guide

Shelter Island is a charming town just a stone's throw away from the bright lights of New York City. While the area is very quiet, there are still activities to enjoy if you are willing to scratch beneath the surface.

Things to Do in Shelter Island

One of the best things to do in Shelter Island is to enjoy the beaches scattered throughout the region. Many of these are quiet and secluded, often feeling as though you have landed on a private beach. A local favorite is Crescent Beach.

For hiking trails, head over to the 2,000 acre Mashamock Preserve.

Best Time to Visit Shelter Island

The best time to visit Shelter Island is during the summer, at which time the temperatures are highest and perfect for beach activities.

Price and Availability in Shelter Island

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Shelter Island tends to be Thursday, while the most expensive day tends to be Saturday. Vacation homes in Shelter Island tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Shelter Island is in August, while the cheapest month is in October. The most popular time to book a vacation rental in Shelter Island is in the high season in August. Shelter Island has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Shelter Island

Rainy days
88°
5
88° -3°
3
63°
3
99° 10°
7
84° 35°
5
90° 35°
3
97° 53°
3
88° 47°
2
80° 35°
1
129° 30°
6
69° 13°
3
58° 10°
7
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Shelter Island. The warmest months in Shelter Island are March and September, when temperatures reach 129 ˚F. The coolest month is November, when temperatures drop to -3 ˚F. The wettest month in Shelter Island is January with 7.02 inches of rain, while the driest month is April with 1.1 inches of rain.

What Expert Travelers Think

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

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