- Style: Classic
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.