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 20 guest rooms that all have private porches looking out onto the water. Like 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, paddle boards, and boats so guests can waterski, fish, or generally explore the area by water. Good to know: Since the beach here is west-facing, it's a great place to watch the sunset.
23 Grand Ave., Shelter Island Heights
After a grand re-opening 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. The rooms are equipped with all the amenities you'd want, without sacrificing any of the charm of this 121-year-old property. Like a proper inn, breakfast is served every morning in the beautiful lobby. But if getting up sounds like too much work, they'll serve you coffee and pastries in bed. Red Maple, the hotel's full-service restaurant, serves weekend dinners and an a great Sunday brunch on a patio that overlooks the water. For something lighter, White Hill Cafe has great pastries and sweets (ask them to put together a to-go picnic before heading to the beach) and connects to Jack's Stir Brew coffee bar.
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