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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
75° 15°
6
60° 8°
7
67° 6°
2
55° 3°
3
64° 16°
4
62° 20°
4
81° 26°
1
86° 33°
2
93° 29°
2
89° 19°
4
86° 32°
2
73° 20°
7
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Shelter Island. The warmest months in Shelter Island are June and May, when temperatures reach 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

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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!

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  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

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