Omni Parker House Rating: 3.5 Pearls
In a city that wears its historic pedigree like a badge of honor, the Omni Parker House has a lot to boast about. Opened in 1855, the 551-room landmark is the longest continuously operating hotel in the country, and the first in Boston that offered running water and elevator service. The hotel's famous guests -- and former employees -- read like a laundry list of the political and cultural elite: Charles Dickens frequently stayed at the Parker House during his trips to the U.S., and it was here that he did the very first reading of "A Christmas Carol" on American soil for members of the Saturday Club literary group. Decades later, Ho Chi Minh worked as a baker in the basement kitchen, likely churning out the hotel's deservedly famous, eponymous Parker House Rolls. J.F.K. proposed to Jackie at a table at Parker's Restaurant, where Malcolm X once worked as a busboy. To hear about the hotel's spookier history, ask old-timer concierge Seamus Murphy about the ghost of the 19th-century whiskey salesman who lives in the closet of room 303, and plants booze-soaked kisses on female guests.
Liberty Hotel Rating: 4.0 Pearls
For nearly 150 years, the tall granite building at 215 Charles Street was known as the Charles Street Jail and housed some of Boston's most heinous criminals. In 2007, after a painstaking restoration that preserved elements of the original design (including the jail's iron bars), it reopened as the Liberty Hotel.
The Fairmont Copley Plaza Boston Rating: 4.5 Pearls
Just as palatial as it was when it first opened in 1912, the storied 383-room Fairmont Copley Plaza remains as iconic to Boston as the Plaza is to New York -- and no less grand, as they share the same architect. The lobby alone is 5,000 square feet, with 21-foot-high gilded, coffered ceilings. The sumptous, wood-paneled Oak Bar and Oak Room are as grand as the rest of the hotel and give guests a taste of a different era (literally -- Clams Casino, a dish which gained popularity in the 1920s, still makes it onto the dinner menu). "Boston's Grand Dame" has welcomed every major U.S. president since Taft, every celebrity from Frank Sinatra to Tom Cruise, and more than a few of the world's most powerful moguls -- like Sumner Redstone, who famously survived the hotel's tragic 1979 fire by hanging from a third-story window. (The fire was set by a disgruntled former employee and injured 30 people, one of whom later died.)
The Lenox Hotel Rating: 3.5 Pearls
Constructed in 1900 as the most luxurious hotel in New England, the charming Back Bay hotel has welcomed guests for over a century to its 214 rooms on the corner of Boylston and Exeter Street -- a prime location just a block from Copley Square and with bird's-eye views of the Boston Marathon finish line. Black-uniformed porters welcome guests into the elegant yet comfortable lobby, accented by marble floors, ebony reception desks, and a wood-burning kept roaring all day (there's a fireplace in a quarter of the rooms as well) -- often tended to by Jimmy, the Lenox's cherished bellman for over 60 years.
Marriott's Boston Custom House: A Marriott Vacation Club Resort Rating: 3.5 Pearls
Only in Boston will you find a Marriott Vacation Club housed in a landmarked building with a history that dates back to the mid-19th century. The building was erected in 1847 and functioned as, well, a custom house, serving as a point of entry for clipper ships and collecting duties on imported goods. Up until the mid-20th century, it was the tallest building in Boston, and its clock tower is still a distinctive feature of the city's skyline. A small museum dedicated to the hotel's history is located in the rotunda on the 2nd floor.
The Copley Square Hotel Rating: 3.5 Pearls
The landmarked Copley Square Hotel, opened in 1891, is the second-oldest operating hotel in the country. It has hosted everyone from Babe Ruth to President McKinley, and Billy Holiday sang at the hotel's now defunct famous jazz club, Storyville. The $18 million renovation in 2008 unfortunately didn't honor the property's past, but history buffs can head to the Freedom Trail, a 2.5-mile red-brick path to 16 historically significant sites, which begins only a few blocks away.
Loews Boston Back Bay Rating: 4.0 Pearls
It's hard to imagine that the homey, 225-room Back Bay Hotel, with its cozy, comfortable rooms was ever an office building where the work centered around gritty crimes and hardened criminals -- but that's exactly what it was. Built in the 1920s, the hotel building was Boston's police headquarters throughout the last century. The cheeky name of the bar, Cuffs, and the lobby's black-and-white photographs from its days as police headquarters pay homage to the property's past. Engraved letters on the building's stone exterior still read: "City of Boston Police Department Headquarters."
Langham Hotel Boston Rating: 4.0 Pearls
Overseas, the Langham name is synonymous with old-world luxury. The brand dates back to Victorian England, and indeed, a certain regal, old-fashioned elegance pervades the tony marble lobby of the Boston outpost, from the dark velvet furniture and China cabinets in the lobby to the original paintings by famous 20th-century American artist N.C. Wyeth and the framed antique maps that hang in some of the banquet rooms. Vestiges of its former life as a Federal Reserve bank are subtly present throughout the 1922 property. The bank's original iron seal was unearthed from the floor during a recent renovation of the hotel's stylish eatery BOND, and all of the guest rooms located on the 2nd floor, where the bank's main lobby used to be, have soaring ceilings. Hallways are lined with antique black-and-white photos depicting the building's banking past.