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Shelter Island Vacation Rentals

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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.

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Price and Availability in Shelter Island

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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.
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The Weather in Shelter Island

Rainy days
89° 31°
4
87° 40°
1
90° 47°
5
92° 52°
4
83° 43°
5
77° 33°
6
68° 15°
2
60° 16°
1
53° 7°
2
54° 5°
3
72° 15°
3
72° 19°
4
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
Rainy days

This climate histogram shows you the weather patterns in Shelter Island. The hottest month in Shelter Island is May, when temperatures peak at 92 ˚F. The coolest month is November, when temperatures drop to 5 ˚F. The wettest month in Shelter Island is March with 6.05 inches of rain, while the driest month is July with 1.19 inches of rain.

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What Expert Travelers Think

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
    The Life of a Social Butterfly

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
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  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
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