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Shelter Island

Photo of Shelter Island

About Shelter Island

Lying between the North and South Forks of Long Island, Shelter Island is sometimes called the un-Hamptons; it is similar to those well-heeled communities on Long Island but without the glitz and glamour. Around 8,000 acres (four-and- a-half miles long and almost as wide) much of the island is protected wetlands. You come here for the lovely beaches, the laidback lifestyle - more bicycles than cars - and the seafood. The best places to stay on Shelter Island let you enjoy all three.

You could just hang out on one of the pristine beaches, but to get more out of the island, hire a bike and explore the many cycling trails. The southern part of the island is made of the 2,000-acre Mashomack Nature Preserve where you can spot ospreys, herons and egrets. You can also kayak through the tidal creeks, wetlands and salt marshes where you might spot terrapins, too.

Take the ferry over to North Fork where you will find acres of farmland and wineries. Indeed, you will be spoiled for choice as around 30 vineyards are easily reached, many of which are open for tours and wine-tasting.

The best places to stay in Shelter Island are popular during the summer months, so don’t leave it too late to book your stay.

The best hotels in Shelter Island

  • The Sunset Beach Hotel couldn’t get closer to the beach after which it is named. Fun and lively, the hotel has popular al fresco dining while its 20 rooms are cool and crisp with hardwood floors and private sundecks. A favourite hangout of the glamorous from the nearby Hamptons.

For more choices, browse our list of the best places to stay in Shelter Island, expand your search to include the Hamptons, Long Island, or New York; or contact one of our friendly gurus for advice.

Best Hotels in Shelter Island

  • Sunset Beach Hotel 20 rooms from $326

    Shelter Island

    Seaside hotel on Shelter Island with spectacular views. A tastefully renovated 1960s motel, the hotel, both intimate and lively, has a popular outdoor restaurant and bar. Each room has a private sundeck, hardwood floors and modern furnishings, and the hotel opens out onto a stunning private beach.

    Active Holiday  -  The hotel can organise biking, kayaking, volleyball, petanque, horse riding, sailing, jet skiing, tennis, golf and fishing.
    Beach Life  -  On the beautiful Sunset Beach, this hotel is the perfect option for anyone looking to bask in the sun by the ocean.
    Views  -  Unobstructed spectacular views of the ocean and the beach from each room.
    Lively  -  Hip and happening.
    Recommended by  -  Tablet, Mr & Mrs Smith
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  • The Chequit 36 rooms from $345

    Shelter Island Heights

    The Chequit, located on Shelter Island Heights, offers spacious accommodation featuring light pink hues, wooden floors, Persian rugs and colourful furniture. Enjoy delicious seasonal dishes at the Red Maple restaurant and soak up the views from the terrace. A chic coastal spot!

    Romantic Break  -  Charming rooms, with rainfall showers, excellent views and knockout food- the ideal romantic getaway.
    Beach Life  -  Head down to Shelter Island Heights Beach Club and lounge on the seashore
    Great walks  -  Take a hike through the stunning Mashomack Preserve, full of beautiful wildlife
    Sailing  -  Island Yacht Charters organise boat trips around the area
    Recommended by  -  Mr & Mrs Smith
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