Find Vacation Rentals in Shelter Island

We have 711 properties to choose from
Shelter Island
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Popular Shelter Island Vacation Rentals

Find the perfect Shelter Island vacation rental

Cottage Shelter Island
$95 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
Details
Details
House Shelter Island
$530 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
Details
Details
House Shelter Island
$237 per night
House ∙ 30 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
Details
Details
House Shelter Island
$515 per night
House ∙ 8 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
Details
Details
House Shelter Island
$894 per night
House ∙ 10 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
Details
Details
Apartment Shelter Island
$239 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
Details
Details
House Shelter Island
$303 per night
House ∙ 8 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
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Details
House Shelter Island
$445 per night
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
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Details
House Shelter Island
$406 per night
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Shelter Island
$540 per night
House ∙ 8 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Pool
Details
Vrbo
Details
Details
House  Shelter Island
$605 per night
House ∙ 8 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Pool
Details
Vrbo
Details
Details
House  Shelter Island
$784 per night
House ∙ 8 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
Pool
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

Apartment  Shelter Island
$287 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Shelter Island, Suffolk County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Shelter Island
$429 per night
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
Cottage  Shelter Island
$364 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Shelter Island, Suffolk County, New York, United States
Pet-friendly
Details
Vrbo
Details
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Best vacation rentals with a balcony

House  Shelter Island
$307 per night
House ∙ 6 guests ∙ 3 bedrooms
Shelter Island, Suffolk County, New York, United States
Balcony
Details
Vrbo
Details
Details
House  Shelter Island
$1,560 per night
House ∙ 6 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
Balcony
Details
Vrbo
Details
Details
House  Shelter Island
$613 per night
House ∙ 8 guests ∙ 4 bedrooms
Shelter Island, Suffolk County, New York, United States
Balcony
Details
Vrbo
Details
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 $96 per night.

How many vacation rentals are available in Shelter Island?

Our large collection of vacation homes makes it easy to filter and compare 709 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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