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Shelter Island Vacation Rentals

Our Favorite Vacation Rentals in Shelter Island

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Shelter Island Pet-Friendly Vacation Rentals

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
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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 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 Weather in Shelter Island

96º 45º
2.67
91º 47º
6.51
90º 44º
4.71
77º 14º
6.29
66º 12º
8.77
60º 12º
5.41
55º -3º
2.64
60º
5.15
60º 16º
5.18
68º 18º
3.6
81º 34º
2.63
89º 37º
1.93
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
This climate histogram shows you the weather patterns in Shelter Island. The hottest month in Shelter Island is June, when temperatures peak at 96 ˚F. The coolest month is January, when temperatures drop to -3 ˚F. The wettest month in Shelter Island is November with 8.77 inches of rain, while the driest month is June with 1.93 inches of rain.

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