Shelter Island Vacation Rentals

Our Favorite Vacation Rentals in Shelter Island

  • Victorian Seasons 5-bedroom Manor
     Country House
    Booking.com
    From
    $1,250
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,574
  • Victorian Seasons Cape
     Country House
    Booking.com
    From
    $650
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $702
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $448
  • Room with own sitting area
     Home/Apartment
    Booking.com
    From
    $140
  • Sag Harbor Perfect For Extended Family and Friends
     5br Home/Apartment
    HolidayLettings
    From
    $3,075

Check prices for these upcoming dates

Shelter Island Vacation Rentals with a Pool

  • Chic Shelter Island Home, Pool and Gardens
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,040
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $325
  • Modern, spacious SI home with heated gunite pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $706
  • Secluded and Sheltered
    Excellent4br Home/Apartment
    Airbnb
    From
    $531

Shelter Island Vacation Rentals with Wi-Fi

  • Three bedroom apartment
    Good3br Home/Apartment
    Airbnb
    From
    $252
  • Two bedroom bungalow with sleeping loft
    Excellent2br Home/Apartment
    Airbnb
    From
    $412
  • Shelter Island Hidden Waterfront
    Excellent3br Home/Apartment
    Airbnb
    From
    $961
  • The Shelter Island Farmhouse
     4br Home/Apartment
    Airbnb
    From
    $942

Shelter Island Pet-Friendly Vacation Rentals

  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • East Hampton Classic
    Excellent4br Home/Apartment
    Flipkey
    From
    $1,136
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $3,026
  • LARGE OPEN SPACE, POOL, PETS WELCOME
     4br Home/Apartment
    HolidayLettings
    From
    $2,405

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 in Shelter Island

Most expensive
Most availability
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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.

The Weather in Shelter Island

Rainy days
66° 12°
9
60° 12°
5
55° -3°
3
60°
5
60° 16°
5
68° 18°
4
81° 34°
3
89° 37°
2
96° 45°
3
91° 47°
7
90° 44°
5
77° 14°
6
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 hottest month in Shelter Island is June, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to -3 ˚F. The wettest month in Shelter Island is February with 8.77 inches of rain, while the driest month is July with 1.93 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — 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
    Alli SimsAlli Sims
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

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