Hidden in Plain Sight

A tranquil harborside retreat, a stone's throw away on idyllic Shelter Island


Browse availabilities, for summer and beyond, on our rentals page


The inn offers individually appointed, fully furnished one- and two-bedroom suites and villas, each with private balcony, ideal for both short- and long-term stays.


The inn sits atop a verdant seven acres overlooking picturesque Dering Harbor, to the North Fork horizon.

Browse our grounds


In addition to the natural surroundings, guests enjoy temperature-controlled open-air swimming pool, access to fitness center and tennis courts, gas grills for outdoor barbecuing, and a fresh-juice and coffee bar, all on the premises.


A ten-minute walk from the North Ferry, the inn is mere steps from the bustling Bridge Street thoroughfare, charming Heights and historic Sylvester Manor, a short walk, bike or car trip to the island’s endless beaches and attractions, and an easy connection to North Fork and transit points west.

Fitness & Wellness

Dering Harbor Inn is home to Moussa Drame Tennis Academy and Shelter Island Yoga & Fitness, boasting a full gym and daily rotation of pilates, spin, and yoga classes. What’s more, the inn is a doorstep to everything that makes Shelter Island a haven, unlike any other, for runners, cyclists, swimmers, hikers and outdoors buffs of all stripes.