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

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What Expert Travelers Think

  • — 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

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    Jeff CampbellMiddle Class Dad
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  • — 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.

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  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
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