Shelter Island Vacation Rentals

Our Favorite Vacation Rentals in Shelter Island

  • Victorian Seasons 5-bedroom Manor
     Country House
    Booking.com
    From
    $1,250
  • Downtown Greenport Apt w/Porch Near Shelter Island
     Home/Apartment
    HolidayLettings
    From
    $290
  • Amazing Beach House Bungalow - Steps to the Beach
     Country House
    Booking.com
    From
    $399
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,116
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $530
  • Sag Harbor Great Loc + Pool
     Country House
    Booking.com
    From
    $475
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641

Check prices for these upcoming dates

Shelter Island Vacation Rentals with a Pool

  • Sunny Country cottage with pool
    ExcellentCottage
    Airbnb
    From
    $203
  • Chic Shelter Island Home, Pool and Gardens
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,040
  • Charming Shelter Island Farmhouse Pool
     3br Home/Apartment
    Airbnb
    From
    $650
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $410

Shelter Island Vacation Rentals with Wi-Fi

  • Three bedroom apartment
    Good3br Home/Apartment
    Airbnb
    From
    $252
  • Family Friendly Island Home
    Excellent4br Home/Apartment
    Airbnb
    From
    $509
  • Shelter Island retreat.
    Excellent2br Home/Apartment
    Airbnb
    From
    $565
  • Beautiful apartment close to everything
    ExcellentHome/Apartment
    Airbnb
    From
    $339

Shelter Island Pet-Friendly Vacation Rentals

  • East Hampton Classic
    Excellent4br Home/Apartment
    Flipkey
    From
    $784
  • Beautiful East Hampton Home w/ Hot Tub & Pool!
     4br Home/Apartment
    HolidayLettings
    From
    $1,047
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $876
  • Hamptons Lofty Beach Barn - Pet Friendly
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $1,288

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
90 º44
5
77 º14
6
66 º12
9
60 º12
5
55 º-3
3
60 º3
5
60 º16
5
68 º18
4
81 º34
3
89 º37
2
96 º45
3
91 º47
7
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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 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

  • — 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
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

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