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Destination guide

Explore the waterfront setting in Shelter Island

The area's history and museums are just a few of the reasons to vacation in Shelter Island. This scenic city is known for its island views, kayaking and parks. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Activities and attractions in and around Shelter Island

Are you looking for things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Shelter Island has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Gardiner's Bay Country Club (2.5 mi / 4 km)
  • Shelter Island Country Club (2.7 mi / 4.3 km)
  • Shelter Island Tennis Club (3.2 mi / 5.2 km)
  • Island's End Golf and Country Club (4.6 mi / 7.5 km)
  • Kontokosta Winery (4.7 mi / 7.6 km)
  • Sag Harbor State Golf Course (4.9 mi / 7.9 km)
Natural features

Exploring the natural features in Shelter Island

Whether you're looking for adventure or just want to appreciate the scenery, Shelter Island is a great place to spend some time outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Mashomack Preserve (0.2 mi / 0.3 km)
  • Wades Beach (1.3 mi / 2 km)
  • Shell Beach (1.8 mi / 2.9 km)
  • Menhadden Lane Beach (2.3 mi / 3.7 km)
  • Sunset Beach (2.9 mi / 4.7 km)
  • Crescent Beach (3.1 mi / 5 km)
How to get there

Traveling to and around Shelter Island

The nearest airport is in East Hampton, NY (HTO), located 7.6 mi (12.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Fishers Island, NY (FID-Elizabeth Field), which is 20 mi (32.2 km) away.

How many vacation rentals are available around Shelter Island?

Our 2020 vacation rental listings offer a large selection of 2,085 house rentals around Shelter Island. From 1,853 Houses to 120 Cabins, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Shelter Island is on HomeAway.

What is the best area to stay when travelling to Shelter Island?

Whether you're travelling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Shelter Island:

  • Silver Beach: 44 vacation rentals
  • Coecles Harbor: 16 vacation rentals
  • Hay Beach: 15 vacation rentals
  • Menantic Creek: 33 vacation rentals
  • The Heights: 32 vacation rentals

For other neighbourhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when travelling to Shelter Island?

HomeAway offers a large selection of lodging choices near lovely places in Shelter Island. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Sylvester Manor: 2,890 home rentals
  • Havens House: 2,916 home rentals
  • Shelter Island Whale's Tail: 2,913 home rentals
  • Mashomack Preserve: 3,014 home rentals
  • Shelter Island Tennis Club: 2,886 home rentals

But there are many other points of interest around Shelter Island listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Shelter Island?

Yes, of course. HomeAway has 1,853 Houses in Shelter Island. Our other popular types of vacation rentals in Shelter Island include:

  • Cabins: 120 lodging choices
  • Cottages: 120 lodging choices
  • Villas: 4 lodging choices

But you can also enjoy a great stay in one of our other vacation homes including Bungalows and more.

Can I find a vacation rental with pool in Shelter Island?

Yes, you can select your preferred vacation rental with pool among our 1,405 vacation homes with pool available in Shelter Island.

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