The Pridwin Hotel & Cottages

Crescent Beach sits right outside the door here, with Peconic Bay stretching out beyond it, and the Pridwin has been around forever. It reads more like an Adirondack lodge than a beach resort, which is either confusing or exactly right depending on your mood. The 49 rooms and scattered cottages have been renovated to keep the old bones while adding a cleaner, more considered feel. Shelter Island itself requires a ferry, which keeps the crowds honest.