Shelter Island Vacation Rentals

Our Favorite Vacation Rentals in Shelter Island

holiday home for max. 8 persons in East Hampton, NewYork

TUIVillasFrom $5977
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Sunny Room in Sag Harbor

Booking.comFrom $300
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Victorian Seasons 1 bedroom Carriage House Duplex
Excellent
HolidayLettingsFrom $487
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Topping Rose House

NextTripFrom $2696
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holiday apartment for max. 12 persons in East Hampton, NewYork

TUIVillasFrom $12403
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Sag Harbor Privacy 6Min Bridgehampton

Booking.comFrom $2000
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Beech Tree Cottage
Excellent
HolidayLettingsFrom $602
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holiday home for max. 16 persons in Bridgehampton, NewYork

TUIVillasFrom $35632
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Shelter Island Vacation Rentals with a Pool

Sunny Country cottage
Excellent
AirbnbFrom $263
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Waterfront carriage house studio
Excellent
AirbnbFrom $399
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Cottage in the Hamptons/Sag Harbor
Excellent
AirbnbFrom $358
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Water's Edge First Floor Condo!

AirbnbFrom $765
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Shelter Island Vacation Rentals with Wi-Fi

★ Shelter Island Retreat ★
Excellent
AirbnbFrom $1405
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Shelter Island- Classic Water-view Beach House
Excellent
AirbnbFrom $554
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Ground floor 1 bedroom apartment close to it all!!
Excellent
AirbnbFrom $347
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Beachfront Room at Ram's Head Inn

AirbnbFrom $643
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Shelter Island Pet-Friendly Vacation Rentals

BRAND NEW Romantic 2br Cottage On YOUR Beach
Excellent
AirbnbFrom $1150
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Midcentury Modern House on 1 Acre
Excellent
AirbnbFrom $891
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Private Sag Harbor/Southampton Home-Pool &Jacuzzi
Good
AirbnbFrom $3326
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Sag Harbor Apartment

AirbnbFrom $385
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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

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

SEE FULL WEATHER FORECAST:

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

60º 12º

5.41

55º -3º

2.64

60º 3º

5.15

60º 16º

5.18

68º 18º

3.6

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

Rainy days

SEE FULL WEATHER FORECAST:

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 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.

What Expert Travelers Think

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Vacation Rentals in Shelter Island

Browse accommodations from all your favorite providers including Airbnb, VRBO, Homeaway and more at AllTheRooms.com. Shelter Island has 192 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. A vacation in Shelter Island can be budget-friendly - our cheapest price vacation rental is available at $10 a night. A typical accommodation in Shelter Island costs on average $974 a night.

If you want an internet connection during your stay in Shelter Island, then you can choose from over 163 accommodations that have WiFi internet. 21 places to stay include a breakfast. Fitness addicts can get a workout in during their stay by choosing from 9 accommodations that have gym facilities. Driving to Shelter Island? Then choose one of the 156 places to stay that comes with a parking spot included. 37 hotels and vacation rentals have a a pool or jacuzzi

If you're traveling with a furry friend, then make sure to choose one of the 47 pet-friendly accommodations available.

In Shelter Island AllTheRooms currently compares hotels, vacation rentals, hostels from more than 4 providers, including 115 places to stay from Airbnb, 18 accommodations from VRBO and 18 places to stay from Homeaway.

145 of our places to stay in Shelter Island have been rated by previous guests. They rated 70% as great. 38 accommodations allow instant booking.