Staying at the Ocean View is like being a guest at a sophisticated house party. Ever since the 1970s, when nineteen-year-old Pip Simmons, a recent graduate of Paris’s Le Cordon Bleu, took over the Ocean View Club, she’s been attracting a rarefied crowd of international media execs and magazine executives and famed photographers like Bruce Weber. Treasures that Simmons has collected on her travels and lots of Irish furniture (they own a house in Ireland as well) adorn the public areas and guest rooms—just as you might find them in the house of an eccentric aunt. Patrons fill the tiny bar at sunset before the call to dinner is sounded, and you might hear tales of some memorable past guests and their legendary antics. Now her handsome son, Ben, is in charge, but the place is still under his mother’s watchful eye. Rooms start at $300. A three-night minimum stay is generally required, but shorter stays may be accommodated based on availability.

Who it’s right for: Anyone who likes the idea of being thrown into a house-party mix. Your fellow guests might include a photo crew on a shoot, a supermodel or a struggling poet.

Who it’s wrong for: Anyone looking for privacy and quiet time and who does not appreciate creative spirits.

Editor’s note: Even if you don’t stay here, try to go for dinner. It’s more like attending an interesting dinner party than going to a restaurant. A few years ago, my husband and I were invited for dinner, and the other guests around the table included the scion of a well-known Southern family and his wife, a famous author and his wife, a charming Dutch photographer and his girlfriend, and Simmonds. We bonded over cocktails and a fantastic meal that we could see being prepared in the adjacent kitchen.—M.B.B.