The Chequit, Shelter Island Heights

The Chequit, inspired by the 1940s, provides guestrooms with premium bedding and free WiFi. The Terrace Suite features a roof terrace with a love seat, and a claw-foot bath in the bedroom. Six rooms are in the Summer House and are more affordable. Six rooms can be made into family rooms with the addition of a day bed for children. Rooms include a mini-bar, parquet floor, and free toiletries. Some rooms provide sea views. All rooms feature two rules: no smoking, and check-out is 11am.

The restaurant, Red Maple, has an expansive terrace for open-air dining. Red Maple serves small bites and traditional mains, including local Montauk fluke and root beer-glazed pork belly. A raw bar offers local oysters and clams. The White Hill Café sells picnic ingredients and hampers as well as coffees, juices and snacks. Red Maple transforms into Mr Crook's Pub, hosting trivia nights along with hearty food. Complimentary breakfast includes fruits, cereals and home-made muesli, muffins and pastries, fresh juices, tea and coffee, served in the lobby and on the terrace. Onsite restaurants include Red Maple.

The Chequit provides a sun terrace and views of the sea. A shared lounge and shops are at the property. A fleet of reconditioned vintage bikes is available to explore the island. The South Street Gallery is 2 km away. Beall & Bell is 2.5 km away. Havens House is 3 km away. East End Seaport Maritime Museum is 2.5 km away. The Village Blacksmith and VSOP Art + Design Projects are 2 km away. Fireboat Firefighter Museum is 2 km away. It is something of a secret compared with the more crowded and better-known holiday towns of the nearby Hamptons.

The Chequit is in Shelter Island Heights, nestling into the North Fork of Long Island. It is a 10-minute ferry journey from Greenport on the north side. Long Island MacArthur is 85 km away. The Long Island Rail Road also runs from New York's Penn Station. The seven-mile island has spacious beaches, picturesque coves and spectacular sunsets.

The Chequit provides concierge services, gift shops/newsstands, and a fireplace in the lobby. The interiors feature chaise-longues and high-backed velvet armchairs in the lobby, and daybeds and oversized potted plants on the wraparound terrace, which faces the nearby harbour. Guests are asked to send information on dietary demands before their arrival.