146+ Rental Villas and Private Getaways in Shelter Island |
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Shelter Island Vacation Rentals & One Degree Stays Homes

About Shelter Island Vacation Rentals

There are more than 146 vacation rentals that are available in Shelter Island. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Shelter Island.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Shelter Island, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Shelter Island. Places to stay near Shelter Island are 909.39 ft² on average, with prices averaging US $1,042 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Shelter Island with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Shelter Island

Type Count
Vacation Homes 117
Holiday Apartments 4
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Shelter Island

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shelter Island.

Weather in Shelter Island, NY

View the weather forecast for Shelter Island before booking your Shelter Island Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Shelter Island, NY

OneDegreeStays offers a large selection of top attractions around Shelter Island. Research things to do on your vacation before you visit Shelter Island.


Mashomack Preserve
Shelter Island Kayak
Wades Beach
Sylvester Manor
Havens House
Shelter Island Historical Society
Cooper's Beach
East Hampton Main Beach
Wolffer Estates Vineyard
Hammonasset Beach State Park
Meschutt Beach
Guild Hall
Ditch Plains Beach
Hither Hills State Park
Clinton Crossing Premium Outlets
The Hamptons Beaches
Orient Beach State Park
Bay Street Theatre
Indian Wells Beach
Ponquogue Beach

Other Places to Stay in Shelter Island, NY


Sylvester Manor 363 Properties
Shelter Island Kayak 305 Properties
Shelter Island Historical Society 222 Properties
Havens House 219 Properties
Menantic Creek 213 Properties
Shorewood 182 Properties
Wades Beach 178 Properties
Mashomack Preserve 174 Properties
Shelter Island Heights 112 Properties

Frequently Asked Questions About Shelter Island?

What are the top vacation rentals in Shelter Island?

There are a lot of options in Shelter Island. If you plan on staying in the Shelter Island area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Shelter Island:

How many vacation rentals have private pools in Shelter Island?

There are 21 vacation rentals with private pools near Shelter Island. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Shelter Island are best for families?

If you are looking for a family-friendly vacation home in Shelter Island, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Shelter Island:

How many onedegreestays vacation rentals are available in Shelter Island?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 146 in the Shelter Island area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Shelter Island. 

Nearby Neighborhood (5) 
Neighborhood Property Count
The Heights Vacation Rentals in Shelter Island, New York 419
Coecles Harbor Vacation Rentals in Shelter Island, New York 293
Menantic Creek Vacation Rentals in Shelter Island, New York 213
Shorewood Vacation Rentals in Shelter Island, New York 182
Montclair Colony Vacation Rentals in Shelter Island, New York 197

People Also Ask

There are 146 Shelter Island, NY Vacation Rentals

Recently Booked Vacation Rentals in Shelter Island