7. Nantucket, Massachusetts
Photography Kate Sears
On this prepossessing New England island, every building appears as though it were created expressly for a storybook, and the hotels, inns, and bed-and-breakfasts are no exception. From quaint shingled cottages to sprawling clapboard guesthouses, each has a personality all its own. The Wauwinet Hotel, pictured above, blends an idyllic, traditional regional setting with luxury amenities.