Set between the North and South Forks of glamorous Long Island, Shelter Island is a wonderfully laid-back destination for an outdoorsy holiday with friends and family or as a couple. Accommodation options are wide-ranging, with everything from contemporary B&Bs to boutique seaside hotels fit for an array of tastes and budgets. Reputedly less glitzy than the nearby Hamptons, the best places to stay in Shelter Island are brilliant for an active, outdoorsy escape.
Just 32 km2 in size, the island is fringed by fantastic beaches, which are ideal for long walks, sandcastle-building or sunbathing. There’s ample opportunity to go swimming, paddle boarding, sailing and wind surfing, too. Head inland to discover meandering cycling trails and hiking paths, as well as the impressive Mashomack Nature Preserve, which covers almost a quarter of the island. These protected wetlands are home to ospreys, herons and egrets — perfect for bird watchers or wildlife enthusiasts. Explore on your own or take a guided tour to learn about the area’s rich biodiversity. The tidal creeks and salt marshes can also be navigated by kayak!
For tours and tastings of fabulous Long Island wineries, take the ferry across to North Fork. The delights of East Hampton and Montauk, on the other hand, are within easy reach by ferry to the south.
Unwind with delicious fresh seafood dinners and lazy evenings gazing up at the stars. On an island with more bicycles than cars, the secret is about embracing the slow life — and the best places to stay in Shelter Island will help you to do just that.
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Shelter Island (New York State)
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.
Shelter Island (New York State)
Classic seaside resort with private beach. Rooms are chic and elegant, the best with water views and private terrace. Cosy cottages offer the same style but a more secluded feel. There's an all-American restaurant & bar plus host of activities for body & soul. A magical beachside retreat.
Shelter Island (New York State)
A charming converted farmhouse B&B not far from the beach on Shelter Island. Elegant, luxurious rooms have contemporary artworks, and large bathrooms with walk-in showers. Breakfast is served in picnic baskets to be enjoyed either in room or out and about! A laid back low-key base.
