Plan for peace of mind

Some properties allow cancellations up to 14 days before arrival. Check the policy before booking.

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Find spaces that suit your style

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Can I find a vacation rental around Shelter Island?

Yes, our 2020 property listings offer a large selection of 2,101 vacation rentals near Shelter Island. From 1,874 Houses to 121 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 HomeAway.

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: 48 vacation rentals
  • The Heights: 29 vacation rentals
  • Menantic Creek: 40 vacation rentals
  • Shorewood: 15 vacation rentals
  • Montclair Colony: 20 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?

HomeAway offers a large selection of vacation rentals 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:

  • Sunset Beach: 2,934 vacation rentals
  • Shelter Island Whale's Tail: 2,970 vacation rentals
  • Gardiner's Bay Country Club: 2,955 vacation rentals
  • Havens House: 2,983 vacation rentals
  • Menhadden Lane Beach: 3,029 vacation 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 1,874 Houses in Shelter Island. Our other popular types of vacation rentals in Shelter Island include:

  • Cottages: 121 rentals available
  • Estates: 20 rentals available
  • Country houses: 12 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Farmhouses 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 1,427 vacation rentals with pool available in Shelter Island. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Shelter Island

    East Hampton
    2,562 vacation rentals
    Montauk
    1,242 vacation rentals
    Sag Harbor
    2,409 vacation rentals
    Hampton Bays
    2,021 vacation rentals
    Westhampton Beach
    844 vacation rentals
    Bridgehampton
    1,931 vacation rentals
    East Quogue
    954 vacation rentals
    Water Mill
    1,932 vacation rentals
    Amagansett
    1,563 vacation rentals
    Southold
    688 vacation rentals
    The Village of Southampton
    2,139 vacation rentals
    Old Lyme
    371 vacation rentals
    Mystic
    461 vacation rentals
    Westhampton
    1,071 vacation rentals
    Quogue
    605 vacation rentals
    Clinton
    266 vacation rentals
    Sagaponack
    915 vacation rentals
    Mattituck
    523 vacation rentals
    Madison
    324 vacation rentals
    Old Saybrook
    328 vacation rentals