The Chequit. (Credit: Skye Gillispie) Sailing, shoreline walks and cocktails at Sunset Beach. A Shelter Island getaway is one of the finest ways to spend your time away from home and the office. But those among us not lucky enough to have friends who own property with a guest cottage and dock rights are going to need a place to stay. Luckily the inns and boutique hotels of Shelter Island provide attractive and homey accommodations. From the recently reopened Shelter Island House to The Chequit, the Island’s hottest new inn, you can’t go wrong with a stay at these six properties. Shelter Island House Style: Sophisticated Recently refurbished and located near Crescent Beach, The Shelter Island House has eight beachy rooms with garden views. The hotel offers a french bistro menu, pétanque courts and even free use of bicycles. Price: Summer rates start at $275 for a Queen Room Perk: Refurbished petanque courts 11 Stearns Point Road Shelter Island Heights (631) 749-1633 Sunset Beach Hotel Style: Trendy Enjoy one of the 20 stylish guest rooms, all with their own private sun deck, water views, seating area and room service from the restaurant. All rooms provide a view of the picturesque Shelter Island sunset. Price: Summer Rates start at around $430 Perk: Complimentary beach chair, umbrella and towels. Free bike and paddle board rentals 35 Shore Road Shelter Island Heights (631) 749-2001 Dering Harbor Inn Style: Private Overlooking the harbor, the Dering Harbor Inn is an intimate place to get away. Stay in one of the inn’s waterfront villas or suites and enjoy its pool, tennis courts, dock and access to the gym at Shelter Island Yoga & Fitness. And it’s just a five minute walk to restaurants and shops. Price: In-season rates start at $330 per evening for a studio Perk: Heated pool overlooking the harbor 13 Winthrop Road Shelter Island Heights (631) 749-0900 The Pridwin Beach Hotel & Cottages Style: Classic Go back in time at The Pridwin and its variety of accommodations. Stay in one of 40 hotel rooms or a cottage with a fireplace. The Pridwin has its own pool and there is a nearby beach lined with chaise lounge chairs. It also offers kayaks, sunfish and paddleboats for use on the bay. Stay on a Wednesday night and enjoy The Pridwin’s famous Wednesday night cookouts. Perk: Water sports vehicles like kayaks, paddle boards and hydrobikes are available for rent Price: Summer rates start at $279 during the week 81 Shore Road Shelter Island (631) 749-0476 The Chequit Style: Modern classic Chances are if you’ve visited Shelter Island, you’ve laid eyes on the grand Chequit inn. Located in the heart of the island, this hotel offers a variety of restored rooms and suites and a magnificent porch. Amentities include the in-house White Hill Cafe as well as surf and skate shop Wampum. And check out the new year-round restaurant, Red Maple. Perk: Complementary and daily changing breakfast menu Price: Summer rates start at $195 for a double room 23 Grand Avenue Shelter Island Heights (631) 749-0018 The Ram’s Head Inn. (Credit: Skye Gillispie) Ram’s Head Inn Style: Traditional Take pleasure in a unique experience at the serene Ram’s Head Inn. Stay in one of 17 rooms, in either a private bath, shared bath or two bedroom suite. Enjoy fine dining with a view of the harbor at the inn’s seasonably focused restaurant. There are also on-site tennis courts, sailboats, kayaks and paddle boards which are all complementary for guests. Perk: Complementary waterfront yoga classes every weekend Price: Summer rates range from $150 per night for shared bath on weekdays to $425 per night for two bedroom suite on weekends 108 South Ram Island Drive Shelter Island Heights (631) 749-0811 Ram's Head Inn 108 Ram Island Dr Shelter Island, NY 11964 … Read More
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