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 being converted to an inn has played host to the likes of John Lennon, John F. Kennedy, and Bette Davis. 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

Rockport is located about 40 miles northeast of Boston along the coast of Massachusetts. The rocky shores here inspired generations of artists, such as Fitz Hugh Lane and Winslow Homer. 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 The Yankee Clipper Inn, Halibut Point State Park shows off Mother Nature's artistry. Craggy granite ledges descend toward water-filled reservoirs, and there are massive boulders planted on the beach where you can get a good view of the area. 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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