Chatham Bars Inn

If Fitzgerald had created Jay Gatsby today, he might have installed his protagonist at the Chatham Bars Inn. The 1914 hotel’s foyer alone, with its polished floors and columns, is irreproachably classy. Still a place where old New England summers, the property encompasses 25 acres, four restaurants, a spa, and more than 210 guest rooms and cottages (a handful of which sit on bluffs overlooking the Atlantic).