We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

Destination Photo

Shelter Island Vacation Rentals

What our users think

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 Index in Shelter Island

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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

60º 16º
5.18
68º 18º
3.6
81º 34º
2.63
89º 37º
1.93
96º 45º
2.67
91º 47º
6.51
90º 44º
4.71
77º 14º
6.29
66º 12º
8.77
55º -3º
2.64
55º -3º
2.64
60º
5.15
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
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.

Vacation Rentals in Shelter Island

Browse accommodations from all the best providers including Airbnb, VRBO, Homeaway and more at AllTheRooms.com. We have 192 vacation rentals, hotels and other accommodation types in Shelter Island ranging from budget options to luxury places to stay. For those traveling on a budget, the cheapest place to stay in Shelter Island is available at $25 per night. On average, a place to stay in Shelter Island will cost you $994 per night.

If you need an internet connection during your stay in Shelter Island, then you can choose from over 163 places to stay that provide WiFi internet. We have 20 accommodations that come with a breakfast included. Fitness addicts can get a workout in during their stay by choosing from 9 accommodations that have gym facilities. If you're planning on arriving in Shelter Island by car, be sure to choose from 156 accommodations that provide parking. 35 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 48 pet-friendly accommodations available.

In Shelter Island AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 4 providers, including 114 places to stay from Airbnb, 18 accommodations from VRBO and 18 places to stay from Homeaway.

147 of our places to stay in Shelter Island have been rated by previous guests. They rated 71% as excellent or good. You can instantly book any of 40 places to stay right now.