Destination guide

Explore the waterfront setting in Shelter Island

The area's history and museums are just some of the reasons to come on holiday to Shelter Island. This scenic city is known for its island views, kayaking and parks. A holiday 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 holiday 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 centre:

  • 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 centre:

  • 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

Travelling to and around Shelter Island

The nearest airport is in East Hampton, NY (HTO), located 7.6 mi (12.2 km) from the city centre. 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 holiday rentals are available around Shelter Island?

Our 2019 accommodation listings offer a large selection of 2,562 holiday lettings around Shelter Island. From 2,253 Houses to 144 Cabins, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Shelter Island:

  • Silver Beach: 47 holiday homes
  • Coecles Harbor: 18 holiday homes
  • Hay Beach: 15 holiday homes
  • The Heights: 35 holiday homes
  • Menantic Creek: 38 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Shelter Island?

HomeAway offers a large selection of holiday accommodations near great places in Shelter Island. From HomeAway travellers, the most popular points of interest to stay near are:

  • Wades Beach: 3,538 holiday lettings
  • Havens House: 3,532 holiday lettings
  • Shell Beach: 3,522 holiday lettings
  • Mashomack Preserve: 3,632 holiday lettings
  • Shelter Island Whale's Tail: 3,529 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Houses in Shelter Island?

Yes, of course. HomeAway offers 2,253 Houses in Shelter Island. Our other popular types of Shelter Island holiday rentals include:

  • Cabins: 144 self catering accommodations
  • Cottages: 144 self catering accommodations
  • Villas: 20 self catering accommodations

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

Can I find a holiday accommodation with pool in Shelter Island?

Yes, you can select your preferred holiday accommodation with pool among our 1,627 holiday homes with pool available in Shelter Island. Please use our search bar to access the selection of holiday rentals available.

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