AllTheRooms.

Shelter Island Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. New York
  4. Shelter Island

Check prices for these upcoming dates

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.

More+

Price and Availability 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 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.
More+

The Weather in Shelter Island

Rainy days
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
88° 47°
2
80° 35°
1
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Shelter Island. The hottest month in Shelter Island is March, when temperatures peak at 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.

More+

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

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

  • — 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

    Whitney Wear
    Whitney WearTravel Better Guide
    Travel Better Guide

  • — 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
    Daniella FloresILIKETODABBLE
    Visit ILIKETODABBLE

Destinations near Shelter Island

  • New York14,756 Properties
  • Brooklyn9,498 Properties
  • Niagara Falls4,147 Properties
  • Queens2,688 Properties
  • Montauk1,493 Properties
  • Lake Placid1,461 Properties
  • Ithaca1,445 Properties
  • Sag Harbor842 Properties
  • Rochester811 Properties
  • Amagansett793 Properties
  • Lake George Village769 Properties
  • Hampton Bays712 Properties
  • Springs700 Properties
  • Southampton699 Properties
  • Ellicottville682 Properties
  • Albany592 Properties
  • Hunter585 Properties
  • Hudson561 Properties
  • Village of East Hampton543 Properties
  • Saugerties542 Properties
  • Woodstock520 Properties
  • Cooperstown510 Properties
  • Windham504 Properties
  • Chautauqua476 Properties
  • Lake George462 Properties
  • Ocean Beach450 Properties
  • Canandaigua443 Properties
  • Geneva433 Properties
  • Bridgehampton419 Properties
  • Saranac Lake403 Properties
  • Penn Yan382 Properties
  • Beacon380 Properties
  • Kingston370 Properties
  • Hammondsport357 Properties
  • Wilmington352 Properties
  • Noyack349 Properties
  • Cherry Grove338 Properties
  • Watkins Glen337 Properties
  • Yonkers332 Properties
  • Staten Island331 Properties
  • Syracuse329 Properties
  • Watermill318 Properties
  • Buffalo306 Properties
  • Chestertown296 Properties
  • New Paltz294 Properties
  • East Quogue291 Properties
  • Alexandria Bay287 Properties
  • Greenport285 Properties
  • Southold274 Properties
  • Long Beach265 Properties
  • Queensbury265 Properties
  • Bolton Landing265 Properties
  • Warrensburg255 Properties
  • Wainscott246 Properties
  • Old Forge243 Properties
  • North Creek242 Properties
  • Cortland233 Properties
  • Binghamton227 Properties
  • Plattsburgh224 Properties
  • White Plains222 Properties
  • Auburn222 Properties
  • Catskill222 Properties
  • Rhinebeck220 Properties
  • Westhampton218 Properties
  • Westhampton Beach215 Properties
  • Poughkeepsie211 Properties
  • Skaneateles206 Properties
  • Trumansburg205 Properties
  • Pulaski198 Properties
  • Saratoga Springs195 Properties
  • Amherst183 Properties
  • Dundee171 Properties
  • Clayton165 Properties
  • Schroon Lake164 Properties
  • Quogue157 Properties
  • Newburgh141 Properties
  • Mount Vernon124 Properties
  • Fire Island119 Properties
  • Tupper Lake107 Properties
  • Diamond Point98 Properties
  • Fleischmanns91 Properties
  • Fishkill90 Properties
  • Millbrook67 Properties
  • Riverhead60 Properties
  • Ellenville59 Properties
  • Chatham56 Properties
  • City of Gloversville53 Properties
  • Port Jefferson40 Properties
  • Findley Lake38 Properties
  • Croton-on-Hudson38 Properties
  • Adirondack33 Properties
  • Sodus Point31 Properties
  • Washingtonville20 Properties
  • Star Lake11 Properties