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9 Historic Hotels With Interesting Past Lives

If these historic hotels could talk, we're sure they'd have a whole lot to say. From converted Neolithic caves in Italy to a female-run brewery turned boutique stay in San Antonio, here are 9 properties with ultra interesting past lives.

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

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The Liberty Hotel, Boston, MA

Ask a local and they’ll probably be able spill a whole lot about the historic Liberty Hotel. The Boston Granite style building was an operating jail until 1990, after all. Built in 1851, the Charles Street Jail imprisoned some pretty high-profile felons – including Malcolm X – within its 220 cells. But by 1990, after decades of complaints from prisoners over poor living conditions, the jail was shuttered, and by 2001, it was being converted into a 298-room luxury hotel with Charles River views. Pop by today and you’ll find that the Beacon Hill stay has done much to preserve its past. You’ll still find the jail’s iconic rotunda, soaring atrium, wrought-iron bars, and exercise yard – a manicured courtyard, in its current incarnation.

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Later this year, the LIFE Hotel will be giving LIFE magazine’s former Herald Square HQ a second chance at Golden Age glory. The NoMad boutique will open in April and feature 90-something rooms done up in 1920s-style decor, honoring the Beaux-Arts building’s past. Prior to becoming the LIFE Hotel, the former office also functioned as writers’ and editors’ apartments, a speakeasy, and the Herald Square Hotel.

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Ace Hotel Pittsburgh, PA

The Ace Hotel brand has a thing for locally-inspired design – just ask its 9 outposts, all of which capitalize on their building’s rich history and architecture. One of the more recent additions, Ace Hotel Pittsburgh, remains true to the brand’s ethos by cozying up in a five-story former YMCA building. Working off of the boys' club’s existing foundation, it features original terrazzo flooring, a grand wrought-iron and marble staircase, original wainscoting and moulding, and a three story gym (two indoor track levels hover above the main floor) replete with restored murals.

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The Fullerton Hotel Singapore

The Fullerton Hotel Singapore has quite the consequential history. Previously the Fullerton Building – which housed Singapore’s General Post Office, the exclusive Singapore Club, and the Chamber of Commerce – the monolithic structure harbored British soldiers during World War II and bore witness to discussions between generals of surrendering Singapore to the Japanese. In converting the enormous space into a heritage hotel in the late 90s, architects retained and restored nearly all of the stately building’s Neo-classical touches. Guests will still find interior and exterior colonnades, soaring verandas, and a portico which dons the original Royal Coat of Arms.

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Hotel Emma, San Antonio, TX

Hotel Emma’s namesake was pretty badass. But in order to fully appreciate that, first you have to know that the property used to be Pearl’s Brewhouse – a business that took up operations in a circa-1894 Second Empire style building under the direction of Otto Koehler. When Koehler passed in 1914, his wife, Emma, assumed CEO responsibilities and successfully led Pearl’s through Prohibition – the only San Antonio brewery to pull of such a feat – by putting the hush-hush on beer production and the full-steam-ahead on dry cleaning and auto repair. Following the brewery’s closure in 2001, more than 68 years after Emma relinquished her post, accommodations reflect the original brewhouse’s industrial design while throwing in some San Antonio style.

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Sextantio Le Grotte della Civita, Italy

When we say that Sextantio Le Grotte della Civita’s history goes way back, we mean back to the prehistoric period. What now makes up the luxe hotel are remnants of one of the oldest Neolithic settlements in Italy, a remote cliffside collection of limestone caves that sit on the fringe of Matera village, in Sassi area. Over the centuries – from the Stone to Bronze age – the caves of Sassi have housed generations of monastic orders and farming communities. When Sextantio came along in 2009, designers wisely allowed the dramatic setting takes precedence which meant outfitting the caves with super minimalist furnishings (opting for pieces made of recycled materials) and hiding light fixtures from view.

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Nashville Union Station Hotel, Nashville, TN

While the 19th-century Union Station railway terminal first debuted as a luxury hotel in 1986, it re-wowed everyone last year as it came fresh off of a $15.5 million renovation. The Victorian Romanesque Revival style station, which had originally opened in 1900, had been a doozy of Italian marble, ornate interiors, and stained glass. Coming out of its various revamps – including the most recent – designers always ensured that guests stepping foot in the hotel would be brought back to the once-glamorous nature of train travel. Need evidence? Just check out the oak doors, limestone fireplaces, and 65-foot vaulted atrium done up in century-old stained glass and gold-leaf detailing.

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The Merchant Hotel, Belfast, UK

In it’s second life, the High Victorian building at 16 Skipper Street – in Belfast’s Cathedral Quarter – may be a luxury hotel, but in its heyday, it was the headquarters of Ulster Bank. Quick to reveal the hotel’s commercial past are surviving architectural accents like ornate Corinthian columns, an imposing central dome, and a sculptural facade. Today, rooms are split design-wise between Victorian (located in the original building) and Art Deco (in the 2010 addition).

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21c Museum Hotel Oklahoma City, OK

Flit along downtown OKC’s Film Row – once home to some of Hollywood’s biggest studios (think MGM, Warner Bros, Paramount Pictures) – and you’ll happen across the sixth edition of 21c Museum hotels. Set in the original Ford Motor Company Assembly Plant, when the boutique property (and free to the public exhibition hall!) was no more than a blueprint, it was decided that the space would do more than preserve the defining architectural characteristics of the factory, but incorporate nearly every original detail including the original, light-filled open floor plan, enormous windows, untouched terrazzo flooring (formerly in the Model T showroom), freight elevator doors, and authentic marquee.

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