Ocean House Lead
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Crossover superstar (and street-style icon) Taylor Swift earned serious prepster bonafides when she bought a house in WASP-y Watch Hill, Rhode Island a couple years back. A town of whale-watching and thin-wale corduroys, the small enclave came into its own in the late 19th century as a summer retreat for the upper crust—but one decidedly less fancy than nearby Newport. Wealth in Watch Hill is extreme, but discreet: that guy in the threadbare yellow sweater driving a Jeep with 200,000 miles on it may very well be a billionaire. It's an attitude that fits well with Swift's own down-to-earth m.o.

Still, you don't have to own a 10-bedroom Victorian cottage to steep yourself in the glamour of the region. Among the most storied hotels in the area, Ocean House, is a stone's throw from Swift's residence and has been welcoming the rich and famous for 135 years (it was even the setting for the Douglas Fairbanks silent film American Aristocracy).

A weekend at this boîte of a hotel includes everything you'd expect to come with A-list cred: fluffy beds, cocktails on the terrace, and cabana boys delivering sunscreen, towels, and lunch—as well as a top-rated spa and restaurant. Bonus: The wifi is strong enough to let you binge on Orange is the New Black from your lounge chair (how decadent is that?).

With rooms starting at $805 a night, Ocean House is pricey, no question, but you get serious bragging rights if you happen to run into Swift piggybacking on boyfriend Calvin Harris's back at the beach. Her house is, after all, directly next door.