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.

The Best Places to Stay on Shelter Island

For a Seaside Stay

• The Sunset Beach Hotel is a funky beachfront hotel with 20 relaxing, retro-inspired rooms. Expect private sundecks, white-on-white interiors with pops of orange, and delectable al fresco dining at the onsite eatery. Cycle around on complimentary bikes, play beach volleyball, or go kayaking as a family. A favourite holiday hangout.

For a Tranquil Escape

• Seven is a tranquil converted farmhouse B&B with just seven guestrooms, featuring bold artwork and elegant contemporary decor. Breakfasts come in big picnic baskets, the beach is within easy reach, and there's lots to explore on the island. An intimate base for couples or families.

FOR A HOLIDAY COTTAGE

• If you'd prefer a self-catering option, we suggest that you visit our online partner Booking.com.

TRAVEL INFORMATION

• Fly to New York City and take a train, bus or taxi to Greenport from there. The journey takes just over two hours, ending with a short ride on the North Ferry from Greenport to Shelter Island. Alternatively, drive to New Haven and catch the South Ferry to Shelter Island.
• If you would like to hire a car, we suggest that you contact our online partner Rentalcars.
• For warm days, visit Shelter Island between June and August when temperatures peak at around 26°C and there’s plenty to do outdoors. This is, however, the busiest time of year — time your trip for September or October for tranquility without the crowds. Shelter Island is also a cosy winter destination.

STILL NOT SURE?

• Expand your search to include all the best places to stay in Sag Harbor.
• Alternatively, see our pick of the best places to stay on Long Island.
• Or contact one of our friendly Gurus for advice.

Weather

Monthly Weather in Shelter Island