Sleep where many locals wish they did: on a charming, tree-lined block in the increasingly desirable South End. Encore Bed and Breakfast (from $180) squeezes sleek Italian furniture into a traditional, brick-walled townhouse. Of the four guest quarters, opt for the top-floor Albee Room and enjoy skyline views from the private terrace.
Another option in the South End: Clarendon Square (from $165), a gut-renovated, nineteenth-century townhouse with all the requisite tech toys—flat-screen HD TVs, DVDs, surround sound, and wi-fi.
Across town, be among the first non-convicts to spend the night at the Liberty Hotel (from $295), which opens this month in the granite fortress of the former Charles Street Jail. A few preserved cells are tucked into the lobby, while original catwalks connect the upper floors. Rooms in the top nine stories of the crystalline tower—a new addition to the landmark building—have great views of surrounding Beacon Hill and the Charles River.
Take advantage of some outrageous extras—the complimentary chauffeured Lexus, for example—at Fifteen Beacon in Beacon Hill. The boutique hotel’s sharply appointed rooms (from $325) have contemporary furniture by Dennis Miller and Eric Brand (plus flat-screens in the bathrooms), while the modernist, black lobby sits beneath a giant Jules Olitski abstract painting.