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.

Shelter Island 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 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

57º -9º
3.51
64º 10º
1.18
59º
5.13
83º 21º
3
86º 28º
4.98
93º 38º
3.43
91º 50º
2.17
87º 46º
2.4
85º 39º
2.19
79º 30º
6.36
72º 17º
2.71
59º
1.93
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days
Powered by:

This climate histogram shows you the weather patterns in Shelter Island. The warmest months in Shelter Island are July and June, when temperatures reach 93 ˚F. The coolest month is January, when temperatures drop to -9 ˚F. The wettest month in Shelter Island is October with 6.36 inches of rain, while the driest month is February with 1.18 inches of rain.

Vacation Rentals in Shelter Island

Browse accommodations from all the best providers including Airbnb, VRBO, Homeaway and more at AllTheRooms.com. Shelter Island has 195 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those traveling on a budget, the cheapest place to stay in Shelter Island is available at $66 per night. The average price of accommodation in is $1300 per night.

Those looking to get some work done during their trip to Shelter Island can pick from 164 places to stay that provide WiFi. 22 places to stay include a breakfast. Choose from 9 places to stay that provide gym facilities, so you won't miss a single workout. Driving to Shelter Island? Then choose one of the 157 places to stay that comes with a parking spot included. 36 accommodations come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 46 accommodations that are designated as pet-friendly.

We combine a wide variety of Shelter Island accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 112 places to stay from Airbnb, 43 accommodations from VRBO and 18 places to stay from Homeaway.

147 of our accommodations in Shelter Island have been reviewed and rated. 71% are rated excellent or good. 34 places to stay in are instantly bookable.

Destinations near Shelter Island

Our providers