Sunset Beach, Shelter Island, New York $$$$
Concierge.com's insider take:
This stylishly retro Shelter Island property is owned by famed boutique hotelier André Balazs of New York's Mercer, L.A.'s Chateau Marmont, and the Standard hotels. Each of the 20 rooms is decked out in mod furniture and white-on-white bedding and has a private terrace, complete with lounge chairs and a view of Crescent Beach and Shelter Island Sound. From Memorial Day to Labor Day, guys sporting crisp, untucked oxford shirts and girls in hip-slung jeans and gladiator sandals pack every inch of the hotel's trilevel beachfront hangout. The sunset over the water pairs well with a minty mojito—the potent and pricey cocktail of choice—or a glass of Sunset Beach Reserve (a rosé developed by Balazs and Hamptons vintner Christian Wölffer). Sunset Beach is open seasonally, from the weekend before Memorial Day until September 12.