Where to stay around Shelter Island?

Our 2018 accommodation listings offer a large selection of 2,246 holiday lettings near Shelter Island. From 1,944 houses to 141 cottages, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Shelter Island is on HomeAway.

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
  • Clearwater Beach: 107 holiday homes
  • Barnes Landing: 45 holiday homes
  • Saybrook Manor: 36 holiday homes
  • Niantic: 35 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:

  • Menhadden Lane Beach: 3,123 holiday lettings
  • Cooper's Beach: 3,139 holiday lettings
  • Gardiner's Bay Country Club: 3,121 holiday lettings
  • Amelia Cottage Museum: 2,938 holiday lettings
  • Hither Hills State Park: 2,186 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 1,944 houses in Shelter Island. Our other popular types of Shelter Island holiday rentals include:

  • Cottages: 141 self catering accommodations
  • Farmhouses: 35 self catering accommodations
  • Apartments: 29 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including chateaus 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 1,279 holiday homes with pool available in Shelter Island. Please use our search bar to access the selection of holiday rentals available.

    Make A Holiday Rental House in Shelter Island, USA, Your Home Away From Home

    The Hamptons have long been a popular summer holiday destination for people from New York and beyond, and increasing numbers of foreign visitors are also deciding to take a vacation there. Anyone considering staying in the area, might like to stay in a holiday rental house in Shelter Island. Coming complete with all the mod-cons and comforts of a home away from home, the facilities include a fully fitted kitchen which will prove useful for those people that do not wish to depend on restaurants for every meal. The beautiful, relaxing surroundings are suitable for couples, families or groups of friends alike, and many Americans return not only year after year, but generation after generation.

    Things to Do on Holiday in Shelter Island, USA

    A holiday rental house in Shelter Island is the perfect base from which to enjoy some of the varied leisure activities which the area has to offer. As might be expected by such close proximity to the sea, water sports such as swimming, wind surfing, sailing and fishing are all popular ways to spend time. Other activities include cycling, hiking, tennis, horse riding and golf.

    Places to Visit on Holiday in Shelter Island, USA

    Shelter Island is quite an interesting place to explore, and in fact, much of it is protected wetlands and marshlands. The Preserve area has four official nature trails, which have informative boards describing the area, and present the chance to see some of the local wildlife. For a day trip with a difference, though, a visit to New York City might be in order. A distinct contrast to the quietness of the area surrounding the self catering accommodation in Shelter island, New York is a huge, thriving metropolis. The must-see sights here include the Statue of Liberty, Chinatown, The New York Stock Exchange and the Empire State Building.

    Weather in Shelter Island, USA

    Whilst people do live and work on the island all the year through, a holiday in Shelter Island is best taken during the summer months. The reason for this is that the winters can be long and cold, with snowfall quite common during December and January. Therefore, the months from May through to September are the best time to visit. Daily average highs measure between 23 and 28 degrees Celsius during this time, and rainfall no more than 70mm per month.

    Travel to Shelter Island, USA

    Anyone needing to fly into the Unites States in order to begin their holiday in Shelter Island would be advised to land at JFK airport in New York City. This large complex is the busiest airport in the US with regards to international traffic, and has connections with dozens of different countries around the world. Travellers from the UK can take their pick from a variety of airlines, with perhaps British Airways offering one of the more reliable flights out of London Heathrow (LHR).

    Attractions in and around Shelter Island

    First time in Shelter Island and looking for places to see? Visitors searching for nearby cultural experiences can spend an enlightening afternoon at Havens House, East End Seaport Maritime Museum or Railroad Museum of Long Island. If some outdoor time is on the agenda, soak up some sun at Menhadden Lane Beach and Wades Beach, or experience the natural beauty of Mashomack Preserve. Activities around the area include Gardiner's Bay Country Club, Shelter Island Country Club and Island's End Golf and Country Club. Discover Shell Beach, Shelter Island Whale's Tail or Sylvester Manor while exploring the city during your stay. Why not also add Sunset Beach, Crescent Beach or Shelter Island Tennis Club to your agenda?