Discover a selection of 2,000 holiday rentals in Shelter Island, NY, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 137 per night, and houses and cottages are popular options for a stay in Shelter Island. Either way, you'll find a rental for everyone's needs.
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.

Can I find a vacation rental around Shelter Island?

Yes, our 2020 property listings offer a large selection of 1,850 vacation rentals near Shelter Island. From 1,754 houses to 107 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Shelter Island for a holiday or a weekend are on Vrbo.

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

Whether you're traveling 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: 43 vacation rentals
  • The Heights: 29 vacation rentals
  • Menantic Creek: 29 vacation rentals
  • Montclair Colony: 16 vacation rentals
  • Barnes Landing: 37 vacation rentals

For other neighborhoods, 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 traveling to Shelter Island?

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

  • Havens House: 2,622 vacation rentals
  • Shelter Island Kayak: 2,605 vacation rentals
  • Mashomack Preserve: 2,706 vacation rentals
  • Sylvester Manor: 2,603 vacation rentals
  • Amelia Cottage Museum: 2,430 vacation rentals

But there are many other points of interest around Shelter Island listed on Vrbo UK 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. Vrbo UK has 1,754 Houses in Shelter Island. Our other popular types of vacation rentals in Shelter Island include:

  • Cottages: 107 rentals available
  • Cabins: 107 rentals available
  • Flats: 30 rentals available

But you can also enjoy a great stay in one of our other vacation rentals 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 1,223 vacation rentals with pool available in Shelter Island. Please use our search bar to access the selection of vacation rentals available.

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