Selecting a hotel that enhances your travel experience is a delicate art, much like choosing the right book to bring on vacation. Just as you wouldn’t want to read Anna Karenina on a hot beach in Florida, you wouldn’t want to rest your head in a gleaming high-rise in ancient Peru. Instead, why not opt for a 15th-century conquistador’s manor, set on the training grounds of sacred Incan warriors?
Often a hotel’s history is shorthand for the history of the destination itself. For those who appreciate the idea of property reincarnation, there are buildings all over the world with illustrious past lives—as castles, manors, private residences, industrial mills, monasteries and even prisons—that have since been reimagined as lodgings.
Hotels built to be hotels pack a different punch, hosting legendary guests that contribute to their storied legacies. Lesley M.M. Blume tapped the intrigue of the St. Regis New York in It Happened Here, her limited-edition libretto for Thornwillow Press. The slim volume contains big tales of mustachioed artist Salvador Dalí meeting the wild and wonderful Andy Warhol—and splattering him with paint—as well as style icon Diana Vreeland dancing on a table in a white Chanel dress. The Charlie Hotel, in West Hollywood, was originally built as a haven of bungalows for Charlie Chaplin and his contemporaries to get away from it all. (Today, the Hollywood set uses the refurbished property the same way.) And the story of Raffles, in Singapore, reads like an adventure novel—complete with tigers, escaped prisoners and the finest ballroom in the East.
Whether it’s a grand hotel gilded with gossip or a reconsidered building with a storied past, a historic property offers a mix of understanding and intrigue with an enticing sidecar—by staying there, you become part of its legend. Here are ten of our favorite hotels with history. These walls may not be able to talk, but we certainly can.