Find Vacation Rentals in Shelter Island

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Popular Shelter Island Vacation Rentals

Find the perfect Shelter Island vacation rental

House Shelter Island
from $906 per night
House ∙ 8 guests ∙ 4 bedrooms

265 m² House

5.0
Outstanding(39 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $299 per night
House ∙ 6 guests ∙ 3 bedrooms

130 m² House

4.9
Outstanding(47 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $197 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(5 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $416 per night
6 guests ∙ 3 bedrooms

House

4.9
Outstanding(48 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $948 per night
House ∙ 8 guests ∙ 4 bedrooms

325 m² House

5.0
Outstanding(17 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $789 per night
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

5.0
Outstanding(23 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $389 per night
5 guests ∙ 2 bedrooms

House

5.0
Outstanding(46 ratings)
Shelter Island, Suffolk County, New York, United States
Details
Cottage Shelter Island
from $404 per night
Cottage ∙ 4 guests ∙ 3 bedrooms

84 m² Cottage

4.9
Outstanding(43 ratings)
Shelter Island, Suffolk County, New York, United States
Details
House Shelter Island
from $524 per night
House ∙ 8 guests ∙ 4 bedrooms

260 m² House

4.9
Outstanding(31 ratings)
Shelter Island, Suffolk County, New York, United States
Details
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Vacation rentals and apartments with air conditioning

Cottage  Shelter Island
from $634 per night
4 guests ∙ 3 bedrooms

Cottage

4.8
Outstanding(141 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
Details
House  Shelter Island
from $650 per night
House ∙ 8 guests ∙ 4 bedrooms

225 m² House

4.9
Outstanding(16 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
Details
House  Shelter Island
from $668 per night
6 guests ∙ 2 bedrooms

House

5.0
Outstanding(34 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
Details
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Vacation rentals with a balcony

House  Shelter Island
from $794 per night
House ∙ 6 guests ∙ 2 bedrooms

177 m² House

5.0
Outstanding(4 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
Details
House  Shelter Island
from $358 per night
4 guests ∙ 1 bedroom

House

5.0
Outstanding(6 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
Details
House  Shelter Island
from $1,136 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(29 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
Details
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Vacation rentals with Wi-Fi

House  Shelter Island
from $318 per night
House ∙ 5 guests ∙ 3 bedrooms

149 m² House

5.0
Outstanding(61 ratings)
Shelter Island, Suffolk County, New York, United States
Internet
Details
House  Shelter Island
from $261 per night
House ∙ 6 guests ∙ 2 bedrooms

74 m² House

5.0
Outstanding(17 ratings)
Shelter Island, Suffolk County, New York, United States
Internet
Details
House  Shelter Island
from $3,020 per night
House ∙ 16 guests ∙ 7 bedrooms

604 m² House

5.0
Outstanding(8 ratings)
Shelter Island, Suffolk County, New York, United States
Internet
Details
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Frequently Asked Questions

How much does it cost to stay in Shelter Island?

You can book a vacation rental in Shelter Island for as little as $256 per night.

How many vacation rentals are available in Shelter Island?

Our large collection of vacation homes makes it easy to filter and compare 1,023 offers in Shelter Island.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Shelter Island

Find the best Shelter Island vacation rentals on Tripping.com. With over 257 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Shelter Island range from $140 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 232 homes in Shelter Island offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 124 rentals with pool or jacuzzi, or relax with the family in one of the 225 homes with cable TV. For all those pet owners with dogs or cats, Shelter Island offers 82 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 7 vacation rental sites in Shelter Island where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 202 HomeAway rentals, 16 Booking.com short term rentals and 16 TripAdvisor vacation rentals.

Popular Day Trips Near Shelter Island

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