Art-Deco Mansion on Rocky Bluff Overlooking Atlantic

When New Englanders refer to "the Cape," they of course mean Cape Cod. But Cape Ann, which juts into the Atlantic Ocean about 40 miles northeast of Boston, was colonized first. In fact, its settlement by the English predates the Massachusetts Bay charter by a few years, which is why its residents were called "old planters" and why some of their modern-day descendants retain a proud spirit of independence. On the outermost tip of this rocky, historically rich outcropping stands Yankee Clipper Inn. Situated on a bluff overlooking the Atlantic, the inn offers unobstructed ocean views in all but one of its eight guest rooms.

The art-deco-style mansion was built in 1929, and since its conversion to an inn it's played host to a number of notable guests. John Lennon, John F. Kennedy, and Bette Davis all stayed here at one time or another. The inn makes the most of its location; a wall of windows lines the dining room, and an oceanfront patio is dotted with adirondack chairs, which are also scattered throughout the carefully manicured gardens. All of the rooms featured in this deal are furnished with antiques and come with a private balcony or sitting area for taking in the seascape.

Rockport, Massachusetts: Seaside Town with Artist Colony and State Park

The rocky shores and maritime culture of Rockport inspired generations of artists, such as Fitz Hugh Lane and Winslow Homer. Today, the fishing economy has waned and the granite quarries that gave Rockport its name have disappeared, but the artistic community remains. More than two dozen galleries showcase local and national artists, and the long-standing Rockport Art Association continues to celebrate its 90th anniversary by sponsoring an array of free exhibits and coating canvases in chocolate frosting. Past shows include a retrospective on Harold Rotenberg, a locally born impressionist painter who attended his event's opening at the age of 105.

One mile from Yankee Clipper Inn, Halibut Point State Park shows off Mother Nature's artistry. Craggy granite ledges descend toward water-filled reservoirs, and the massive boulders planted on the beach make good perches for taking in the sights. The park's visitor center—housed in a restored World War II–era fire-control tower—also provides a good vantage point, with a seaward view stretching to Maine's Mount Agamenticus on a clear day.

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