Prisons, Plantations, and More: Hotels with Storied Pasts

For nearly 150 years, this tall granite building 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 prison design, it reopened as the Liberty Hotel. The result is stunning, with nearly 300 rooms, a 90-foot-tall atrium, winding catwalks, and high, circular windows that flood the lobby with light. The hotel’s popular restaurants and bars play on the jailhouse theme with names like Alibi, Clink, and The Yard.

Not surprisingly, Dublin’s Schoolhouse Hotel was once a local schoolhouse, opened in 1859. It has operated as a hotel for nearly twenty years now, and it includes plenty of the historic character as well as literary touches; all rooms are named after a famous Irish writer and have classic decor including floral prints and antiques. The quiet location, excellent food, and history of this hotel make it one of Dublin's best affordable picks.

For a real dose of Brooklyn, it doesn’t get more authentic than The Box House Hotel. This former door factory (random, we know) now houses 57 apartment-style rooms designed by local Brooklynite, Kip Jacobs, who happens to be friends with the owners. The spacious rooms/lofts (some sleep six) attract families, couples and even the occasional film crew. Modern kitchens and free extras include bottled water and coffee, rides within a mile-and-a-half radius, and Wi-Fi.

Adapted from an austere 19th-century courthouse into a hostel-style accommodation with punk sensibility, Clink78 is good value for travelers on a shoestring budget who still like a bit of style. Think street art, neon signs, and bold colors juxtaposed with preserved Victorian judicial details such as witness stands and a magistrate's courtroom that now houses an Internet lounge. The property offers a range of rooms, including mixed dorms, all-women's dorms, and private rooms with en-suite bathrooms.

It’s hard to beat Fond Doux’s level of authenticity. Fruits, spices, and vegetables grow organically throughout the grounds, and on the cocoa plantation -- which dates back to the 18th century -- tours of the process for creating cocoa sticks are given daily. Several of the authentic colonial-style cottages are original 19th-century island structures, and all feature private porches and a romantic, secluded vibe.

This historic landmark is carved from the city’s earliest Whitney Bank branch. The hotel’s single restaurant occupies part of the old bank, which has kept its grand marble pillars, gold-barred teller’s windows, and an original mural (depicting, of all things, a bank robbery) painted along the back wall. Hand-numbered prints with money and banking themes frame the hotel hallways. Beyond its history, the hotel’s big draw is its spectacular location, a block from the St. Charles streetcar and within walking distance of the French Quarter.

This elegant, 78-room boutique hotel is located in the Trastevere neighborhood, a bit far from most tourist sights. Lovers of history will likely appreciate the 17th century monastery setting, designed by a well-known Baroque architect and featuring wood-beamed ceilings, arched hallways, and marble floors. Rooms have antique-style furniture as well as flat-screen TVs, minibars, and spacious bathrooms. The rooftop terrace offers outstanding panoramic views of the neighborhood, and those who want to relax outside can enjoy the pretty courtyard garden.

The 21-room GoldenEye is hands down Jamaica's hippest and most luxurious resort. It's also one of the island's most historic, as the former home of Ian Fleming, and the hideaway at which the author scribed all 14 of his James Bond novels. Today, the property, which reopened in 2010 after an extensive $50 million renovation, includes stunning cottages and villas overlooking a private beach and lagoon, as well as two happening restaurants, two pools, a tree house spa, and an extensive roster of on-site activities.

There are several Kimpton-brand hotels in the District, but the Monaco is the only one in a National Historic Landmark building. The Greek Revival General Post Office, designed by Washington Monument architect Robert Mills and finished in 1839, was reborn as this stylish hotel in 2002. The four-floor property takes up an entire city block on the eastern edge of the Penn Quarter neighborhood, and features small, but modern, rooms and plenty of freebies.

First built in the 13th century, Ashford Castle embodies the fantasy of the Irish castle hotel, featuring a massive historic stone façade, complete with towers and turrets; gorgeous, manicured grounds; a stunning setting on a huge lake; and common spaces that are truly grand, with rich wood paneling, chandeliers, and antique furniture. The wide range of estate activities includes falconry lessons, boat tours on the lake, golf on the 9-hole course, clay shooting, and archery.


RELATED LINKS:

• The 12 Most Romantic Resorts in the Mediterranean
• Worth the View: 12 Budget Hotels with Jaw-Dropping Vistas
• The 12 Best Bed and Breakfasts in the U.S.