Shelter Island Hotels
35 Shore Rd., Shelter Island
Just north of most of the action, Shelter Island remains one of the quieter parts of the Hamptons—cynics would say it's a bit like Montauk in the old days, before real estate values in the area exploded. Owned by André Balazs, Sunset Beach Hotel sidles right up next to the ocean, with just twenty guest rooms that all have private porches looking out onto the water. As at any Balazs hotel, the food (and especially drink) scene is on point, with a great little European-style restaurant and a bar that offers some of the area's best DJs. Easy access to the beach also makes activities blessedly easy here—bikes are complimentary, and the hotel will happily arrange for beach chairs, paddleboards, and boats so guests can water-ski, fish, or just explore the area by water. Good to know: The beach here is west-facing, so it's a great place to watch the sunset.
23 Grand Ave., Shelter Island
After a grand reopening following a major renovation, The Chequit is officially on our Hamptons short-list. The 37-room hotel feels more like a bed and breakfast, which is good since a glitzy resort wouldn't feel at all right on quaint Shelter Island.