Repurposing a historic structure, especially one with a past that is deeply intertwined with its location, is often a gesture of respect and pride. Bringing new purpose to such grand buildings conveys a distinctive sense of place. These 10 extraordinary hotels around the U.S. — reimagined from old factory buildings, long-shuttered nunneries, crumbling city jailhouses, and defunct steel mills — exemplify that idea. One thing you can count on with this list? No two rooms are alike.
The Liberty (Boston, Massachusetts)
From 1851 to 1990, this magnificent stone Romanesque building served as the Charles Street Jail, hosting notorious criminals like Whitey Bulger and one of the participants in 1950’s Great Brink’s Robbery. Because one of the jail’s founders was a clergyman with a deep interest in prison reform, the jail was built with a kinder aesthetic than most. The building, laid out in a cross formation (to separate inmates by gender and seriousness of their crimes), included a soaring 90-foot-tall atrium and 33-foot-tall arched windows to admit light and air. But in the 20th century, the jail fell into such disrepair that not only was it considered inhumane, but some inmates also found it easy to escape.
When it finally closed down, the formidable structure sat unused until it was reimagined — with the participation of architects and historians — as a luxury hotel to the tune of $150 million. That atrium, now the hotel lobby, carries unmistakable elements of its former life — the open walkways around the upper levels, iron-work chandeliers, and access to a couple of cocktail bars called Clink (aptly situated in the old “drunk tank”) and Alibi.
El Convento (San Juan, Puerto Rico)
You can be forgiven for not acting like a saint while staying in the lavish rooms at San Juan’s El Convento. As you can probably guess from its name, the hotel was once a convent for the Carmelite order of nuns. Built in 1651 at the behest of King Phillip IV of Spain, and occupied by nuns until 1903, the building fell into disrepair when they moved out.
Fortunately, the elegant building was not torn down, and in 1962, it opened as a luxury hotel. Its exterior is painted a lemon yellow, and arcaded walkways and flower-laden balconies line its courtyard garden. While contemplative and dignified, the rest of the hotel’s trappings read more romantic getaway than chaste retreat: hand-carved headboards and furniture, wooden beams overhead, and an airy, spacious design that make these guest rooms a blessing indeed.
The Foundry Hotel (Asheville, North Carolina)
This hotel in Asheville’s “The Block” neighborhood comes by its industrial-chic-ness honestly. It was built as a steel foundry, originally meant to manufacture materials for George Washington Vanderbilt’s nearby baronial castle, the Biltmore, and outbuildings on its 8,000-acre property. After the Biltmore was completed in 1895, the mill continued making steel that still supports many landmark buildings in downtown Asheville.
The hotel, which opened in 2018 after extensive (and award-winning) refitting, has retained charming elements of the foundry it once was. Industrial metal signage abounds, and while the scale of the lobby and rooms is fit for large machinery, it makes for an airy hotel instead. Guest rooms have exposed brick walls, high ceilings, and a generous run of paned windows looking out over an open courtyard between the hotel’s sturdy buildings. (However, this outdoor space features fire pits, not forges.)
Chattanooga Choo Choo (Chattanooga, Tennessee)
As its terminally corny name suggests, the Chattanooga Choo Choo’s main Beaux Arts building was originally built to be Chattanooga’s Terminal Station along the Southern Railway line, supplementing service by the city’s Union Station.
After service to the station ended in 1970, the station house and surrounding 25 acres of outbuildings and train yards were re-developed as a hotel and entertainment complex. There’s no mistaking the hotel’s roots as a train station — especially if you book one of the guest rooms that have been built inside refurbished Pullman train cars, stroll through the Glenn Miller Gardens that have been planted between the passenger platforms, or have a drink at one of the bars along Station Street — a nightlife district that has taken hold in the street-facing spaces of the terminal-turned-lobby building.
Chicago Athletic Association (Chicago, Illinois)
When the 1893 World’s Columbian Exposition took place in Chicago, all the newly built monumental architecture wasn’t confined to the fair site on the city’s South Side. This grand Michigan Avenue edifice, designed to resemble the Doge’s Palace of Venice, Italy, was built as a private clubhouse for a certain refined set of gentlemen (think Marshall Field and William Wrigley, both among the founding members), and it served this exclusive crowd until 1972 when women were finally admitted. But membership dwindled towards the end of the 20th century, and the club finally closed in 2007.
The fantastic Venetian Gothic building was reborn as a hotel in 2015 after what the Chicago Tribune called a “spare-no-expense revamp.” Remnants of the building’s sporty history are evident in design elements like benches that look like pommel horses, decorative bar backdrops constructed of pool cues, squash court floors repurposed as elevator panelling, and a game room with shuffleboard and bocce courts.
Craddock Terry Hotel (Lynchburg, Virginia)
Lynchburg, a picturesque college town in the Blue Ridge Mountains, enjoyed a period of prosperity in the late 19th century, as it was home to a variety of mills, foundries, and factories. The largest of these was the Craddock-Terry Shoe Company, once the fifth-largest manufacturer of shoes in the world. At its peak, the company made nearly 100,000 pairs of shoes each day, and it was awarded a government contract for uniform shoes during World War II. Lynchburg’s downtown grew up around the shoe factory and its neighbor, a historic tobacco warehouse, but eventually their business operations were moved outside of the city limits.
The remaining buildings were saved and repurposed (by architect Hal Craddock, the great-grandson of the company founder) into a shoe-themed boutique hotel. When you first see the brick building, you’ll know you’re in the right place: Where other hotels may erect a standard “No Vacancy” sign, the Craddock-Terry has a giant red high heel shoe attached to the exterior instead. The hotel’s decor isn’t pure kitsch, though. In the lobby, displays of stylish vintage shoes honor the building’s history, as do the high wood-beamed ceilings, the generously proportioned tall windows, and the exposed brick walls. Even breakfast is delivered to the guest rooms packed in an antique shoe shine box.
McMenamins Kennedy School (Portland, Oregon)
If you were ever considered a teacher’s pet in school, your inner child would be pleased to find out that you can stay overnight in an elementary school classroom at the Kennedy School in Portland. In the late 1990s, the beloved (but decommissioned and decaying) neighborhood elementary school in Northeast Portland was bought and reborn as a hotel and multipurpose cultural space.
Kennedy School has 35 guest rooms — some complete with chalkboards, murals, rows of coat hooks, and tabletop globes. Of the four hotel bars, one is located in the old detention room and another is down in the boiler room. For more extracurricular activities, there’s also a jazz lounge, a movie theater, and a tiled pool. The family company that renovated the school, McMenamins, specializes in converting historic properties like schools, theaters, and Elk lodges into hotels, music venues, breweries, and bars.
Delta King (Sacramento, California)
There’s no standing onshore and scratching one’s chin, wondering what kind of pre-hotel purpose the Delta King had. The massive, white paddlewheel boat moored on the Sacramento River is exactly that: a stern paddlewheel boat repurposed as a 44-room stationary hotel. The parts for the old steamship were built in Scotland in 1924 then shipped to California for assembly. When the ship was finally seaworthy, it was christened with a sister paddlewheel, the Delta Queen, in 1927. The two sailed the Sacramento River, ferrying well-heeled passengers between San Francisco and the state capital, with shipboard indulgences like gambling, jazz, and drinking (even during Prohibition).
The ships were both drafted into duty as U.S. Navy hospital transport ships during World War II, but after the war, the Delta King was cut adrift. (Her sibling still takes overnight guests on cruises of the Mississippi River.) Found half-sunken in the San Francisco Bay, the Delta King was dried out and refitted for its new life as a hotel, with a permanent address in historic Old Sacramento. A restaurant in the old pilothouse, old-timey furnishings, and shiny brass beds in the staterooms keep the passenger manifest full.
Detroit Foundation Hotel (Detroit, Michigan)
After an unfortunate downturn, Downtown Detroit has enjoyed an ongoing period of revitalization. One example of the creativity fueling it is the 100-room, thoroughly modern Foundation Hotel that inhabits the former Fire Department headquarters, as well as an adjoining building, in high style.
The renovation took advantage of the building’s history. The three arched bay doors where the firetrucks entered and exited were repainted and repaired, and they became the visual focus of the exterior, through which pedestrians can glimpse a busy ground floor restaurant. The architects made molds from the decorative terra cotta elements on the facade — busts of firemen, some gryphons at a fire hydrant — so they could recast them where necessary. Fitting guest rooms into existing spaces in the building required some ingenuity, too: The 100 rooms have 54 different layouts. And while all the modern luxury conveniences are present, so are charming elements from the building’s previous life — like salvaged wood headboards and photos of old Detroit. Local artwork and Detroit-made products are featured throughout the hotel, and checking in feels a bit like joining a city fan club.
Hotel Peter and Paul (New Orleans, Louisiana)
In New Orleans, where piety always exists in proximity with debauchery, the thought of converting a Catholic church and school (plus its associated convent and rectory) into a chic hotel seems almost natural. The 19th-century brick buildings of Hotel Peter and Paul, in the city’s downriver Faubourg-Marigny neighborhood, were gracefully restored and transformed from a little parish hub into 71 guest rooms — plus a bar, lounge, cafe, entertainment venue, and ice cream parlor.
There’s no avoiding the holy history of these structures — heavy swinging hall doors painted a mint green fairly scream “Catholic school," crucifixes are carved into gleaming wood door frames, and frankly contemplative spaces haven’t been masked or repurposed. But nothing feels austere or penitent. Colorful gingham linens, canopied beds, velvet curtains, and carefully selected period antiques of grand scale give rooms a boost of warmth and drama. The gorgeous Elysian Bar, set in the old rectory, is a worthy destination in itself, even in a town full of places to drink.
