4 Best Hotels in Shelter Island, Long Island

In a prime spot on Crescent Beach, The Pridwin was completely renovated in 2012 to create a bright, beachy hip (but not "sceney"), family-friendly resort. It's been around since 1927, with the same family at the helm since the 1950's, and retains some endearing old touches: partially slatted doors that allow air flow (but also some light) into your room; creaky hallway floors; vintage swimsuits and old photos of the property on display. Meals are served on a large waterfront deck, a nice setting for dinner, when piped Brazilian jazz adds to the romantic aura. During the day, Carribbean and classical music is piped throughout the common areas. For the ultimate family party, come on a Wednesday night for the cookout, which can attract around 400–500 locals, guests, and visitors for burgers, hot dogs, and freshly-caught fish.

This 1929 colonial-style inn has a colorful history, including being a 1970s disco with lederhosen-clad dancers, but today it's a peaceful retreat, with staff that makes you feel like family. Tucked away in a secluded spot at the end of Ram Island, its lawns, scattered with Adirondack chairs, slope down to Coecles Harbor with a small and scenic beach for swimming or sailing. Rooms, furnished in simple country style are bright, and special rates and packages are offered throughout the year. The restaurant is known for outstanding seasonal fare and its Sunday sunset jazz dinner (May to late October).

With spectacular views of Dering Harbor, this family-friendly complex just steps from the dock is a perfect base for an active vacation—with many amenities, plus Shelter Island Yoga & Fitness right on-site. Kayaking is available, you can rent bikes, and an outdoor pool and tennis courts are on the premises. Or you can just relax on the peaceful, pleasant grounds and enjoy the water view. Accommodations include motel studios and one- and two-bedroom units; the two-bedroom waterfront suites have a fireplace and private deck.

An international crowd has flocked to this trendy hotel ever since celebrity hotelier Andre Balazs (of Los Angeles's Chateau Marmont and SoHo's Mercer) opened it in the late 1990s. Each retro-style guest room has a sundeck that looks out over the parking lot to the water. The beachfront French bistro–style restaurant provides the best people-watching around, and a great place to relax with a cocktail and enjoy the lingering sunset.