The Chequit, Shelter Island Heights

Guestrooms at The Chequit feature premium bedding, free WiFi, and various layouts including the Terrace Suite, which offers a roof terrace with a claw-foot bath. The six rooms in the Summer House are simply furnished and more affordable, with options to create family rooms by adding daybeds.

The restaurant, Red Maple, presents a selection of small bites and traditional mains including local Montauk fluke and root beer-glazed pork belly. An expansive terrace allows for open-air dining in the summer, while Mr. Crook's Pub provides a cozy British-style atmosphere for trivia nights alongside hearty food.

Guests can take advantage of the shared lounge and shops available on-site. The Chequit promotes outdoor activity with complimentary vintage bikes, allowing exploration of the seven-mile island's beaches and picturesque coves.

Concierge services and gift shops are also offered for convenience. The hotel is accessible via a 10-minute ferry journey from Greenport or Sag Harbor, enhancing connectivity for visitors.