THE CHEQUIT, Shelter Island Heights

The Chequit - A restored Victorian hotel with harbor views, complimentary breakfast, and vintage bicycles

The Chequit offers a restored Victorian property featuring views over the Long Island Sound and nearby harbor. Accommodations include suites such as the Terrace Suite with a private roof terrace and claw-foot bath, while the six rooms in the Summer House provide more affordable options with simpler furnishings. A complimentary breakfast served in the lobby and on the terrace includes freshly baked muffins, pastries, fruits, cereals, and home-made muesli. The restaurant Red Maple serves small bites and traditional mains like Montauk fluke and root beer-glazed pork belly, with an expansive terrace for open-air dining. Evenings transform Red Maple into Mr Crook's Pub, hosting trivia nights and serving hearty food alongside a raw bar offering local oysters and clams. Six rooms can be converted into family rooms with the addition of a day bed for children. A fleet of reconditioned vintage bicycles is available for complimentary use to explore Shelter Island. The property features a shared lounge, gift shop, and fireplace in the lobby. All guestrooms at The Chequit include premium bedding and free WiFi.

Pros

The restored Victorian architecture maintains historic character with modern amenities.

Complimentary vintage bicycles provide convenient transportation for island exploration.

Multiple dining options include Red Maple restaurant and Mr Crook's Pub with trivia nights.

Family-friendly accommodations allow conversion of six rooms with additional day beds.

Harbor-facing terrace offers outdoor dining and relaxation space.

Cons

The property's Victorian layout may not include elevator access to upper floors.

Limited public transportation requires ferry transfers from Greenport or Sag Harbor.