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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
62° 20°
4
81° 26°
1
86° 33°
2
93° 29°
2
89° 19°
4
86° 32°
2
73° 20°
7
75° 15°
6
60° 8°
7
67° 6°
2
55° 3°
3
64° 16°
4
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
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 93 ˚F. The coolest month is November, when temperatures drop to 3 ˚F. The wettest month in Shelter Island is March with 6.94 inches of rain, while the driest month is August with 1.2 inches of rain.

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What Expert Travelers Think

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

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  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
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  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
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