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Shelter Island Vacation Rentals

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Our Favorite Vacation Rentals in Shelter Island

  • Downtown Greenport Apt w/Porch Near Shelter Island
    Downtown Greenport Apt w/Porch Near Shelter Island
     1br Home/Apartment
    HolidayLettingsFrom $306
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  • holiday home for max. 6 persons in Sag Harbor, NewYork
    holiday home for max. 6 persons in Sag Harbor, NewYork
     Country House
    TUIVillasFrom $24625
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  • Victorian Seasons Stirling
    Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettingsFrom $1116
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  • holiday home for max. 14 persons in Southampton, NewYork
    holiday home for max. 14 persons in Southampton, NewYork
     Country House
    TUIVillasFrom $50416
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  • Beautiful French Country Cottage
    Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettingsFrom $530
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  • holiday home for max. 10 persons in East Hampton, NewYork
    holiday home for max. 10 persons in East Hampton, NewYork
     Country House
    TUIVillasFrom $35976
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  • Beech Tree Cottage
    Beech Tree Cottage
    Excellent2br Cottage
    HolidayLettingsFrom $602
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  • holiday home for max. 8 persons in Water Mill, NewYork
    holiday home for max. 8 persons in Water Mill, NewYork
     Country House
    TUIVillasFrom $7791
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See all 200 deals in Shelter Island

Shelter Island Vacation Rentals with a Pool

  • Cliffside Resort! Greenport 2br/2ba Beach Poolside
    Cliffside Resort! Greenport 2br/2ba Beach Poolside
    Excellent2br Home/Apartment
    AirbnbFrom $468
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  • Beach-side Home in Orient w Pool and Lush Garden
    Beach-side Home in Orient w Pool and Lush Garden
     3br Home/Apartment
    AirbnbFrom $523
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  • Quiet Three Bedroom w/ Chef's Kitchen and Pool
    Quiet Three Bedroom w/ Chef's Kitchen and Pool
    Excellent3br Bedroom
    AirbnbFrom $981
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  • Lovely Studio in Sag Harbor Private Entrance
    Lovely Studio in Sag Harbor Private Entrance
    ExcellentHome/Apartment
    AirbnbFrom $266
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See all deals in Shelter Island with a pool

Shelter Island Vacation Rentals with Wi-Fi

  • ★Shelter Island Retreat★
    ★Shelter Island Retreat★
    Excellent2br Retreat
    AirbnbFrom $728
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  • Picturesque waterfront cottage
    Picturesque waterfront cottage
    Excellent2br Home/Apartment
    AirbnbFrom $454
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  • Beautiful apartment close to everything
    Beautiful apartment close to everything
    Excellent1br Home/Apartment
    AirbnbFrom $336
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  • Ground floor 1 bedroom apartment close to it all!!
    Ground floor 1 bedroom apartment close to it all!!
    Excellent1br Home/Apartment
    AirbnbFrom $347
    View Deal
See all deals in Shelter Island with WiFis

Shelter Island Pet-Friendly Vacation Rentals

  • Water View Island Oasis
    Water View Island Oasis
    Excellent1br Home/Apartment
    AirbnbFrom $366
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  • Shelter Island Getaway
    Shelter Island Getaway
    Good3br Island
    AirbnbFrom $550
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  • Shelter Island get away
    Shelter Island get away
    Excellent3br Home/Apartment
    AirbnbFrom $594
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  • Sprawling North Fork Retreat w/Hot Tub & Fireplace
    Sprawling North Fork Retreat w/Hot Tub & Fireplace
    Excellent4br Retreat
    AirbnbFrom $581
    View Deal
See all deals in Shelter Island that allow pets

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 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

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
81º 34º
2.63
89º 37º
1.93
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
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 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

Destinations near Shelter Island