Graycliff Hotel

Grande dame

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During its 230-year lifetime, this National Register of Historic Places landmark has served as a pirate’s home, Anglican Church, headquarters and garrison for the American Navy, one of the earliest plantations worked by freed slaves, inn, Civil War mess hall, private home, and finally in 1973 a family-owned hotel.

Its reputation for fine, five-star, boutique accommodations is surpassed only by its signature restaurant and wine cellar’s fame and popularity among the discriminating.

In 1997, a cigar factory and other expansions brought it to 20 guest rooms, two pools, two restaurants, and a fitness center. In 2012 a chocolate factory, specializing in its dark chocolate tabac, opened. Future plans call for renovating six historic buildings across the street for an artists’ galleries, shops, a coffee-roasting facility, a culinary school, a 75-room hotel, and more.

In the meantime, the house wears its age like a grande dame – some signs of aging here and there but with a near-haughtiness that stays true to her Old World finesse and loyal guests even while seeking ways to win over new clientele.

Each room has its own personality, generally faithful to earlier eras with heavy brocade, antiques, and period trinkets.

In summer, its drafty or flung-open windows can mean a little less cool comfort than some might prefer in the season’s humidity, but Graycliff isn’t for everyone – especially the budget-minded – and doesn’t try or need to be. Its ultimate strength lies in its meticulous service, which trickles down from personalized, steadfast, hands-on family management.

At A Glance

8 W. Hill St.
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