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Hotels in Shelter Island

30 Travelers rated Shelter Island highly for Islands and Whale Watching

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Shelter Island Travel Guide

Shelter Island is a small island located at the eastern end of Long Island, New York. The island was once called “an island sheltered by islands” by the Manhanset Indians. can help travelers book rooms at Shelter Island hotels. Individuals considering traveling to Shelter Island will have a variety of things to do and see, including the deep-water harbors, many shopping opportunities, and fine dining.

South Ferry Road

South Ferry Road is located near the center of the island. Visitors can stay at the Candlelite Inn. Choose from one of the cottages, suites, or private rooms. Rooms start at $195 per night and cottages start at $250 per night. The Candlelite Inn offers private baths, central heat and air, a television in the common room of the Inn, a beautiful wraparound porch, and antique furniture. The cottages each feature a large shower, a double whirlpool, and free wireless Internet. The Inn is located within walking distance of several restaurants and shops on the island. There are also several vineyards in the area that offer tours and wine sampling. The Candlelite Inn is geared toward couples, and all rooms and cottages are nonsmoking. You can contact the Inn at (631) 749-0676 for more information.

Winthrop Road

Located near the Gardiner’s Bay Country Club, the Dering Harbor Inn is located on Winthrop Road. Rooms start at $165 per night for a studio and $375 a night for two bedrooms. Relax and enjoy your vacation with one of several picnic areas, a yoga and fitness center, or the view along the water’s edge. Amenities include uniquely decorated bedrooms, televisions, and private decks, as well as an outdoor swimming pool. The hotel is within walking distance of downtown, where you will find a selection of restaurants, markets, shops, and bars. For more information or to book a reservation, contact the hotel at (631) 749-0900.

Shore Road

Shore Road is located near the island’s west side. Visitors to the area can spend a relaxing vacation at The Pridwin Beach Hotel and Cottages. The hotel is located near the Quinipet Camp and Retreat Center, which offers summer retreats and camp opportunities for both individuals and families. The Pridwin opened its doors in 1927, and it is situated on a 10-acre site on Crescent Beach. The hotel features a lounge with a full-service bar and an on-site restaurant. Room amenities include spacious rooms, private baths, air-conditioning, televisions, and free local calls. The cottages offer king beds, kitchenettes, private decks, and a swimming pool with bay views, and some even have a fireplace. The resort frequently holds cookouts and other events for its guests, and it is a popular spot for weddings. Rooms start at $165 a night, and cottages start at $208 a night. Contact the resort at (631) 749-0476 for more information.

Enjoying Your Stay

Shelter Island is a small island with a lot of character. It features many beautiful hotels and inns from which to choose, and it also offers many fine restaurants and pristine beaches. Use to locate the best deals on Shelter Island hotels and other travel arrangements.