Hidden in plain sight

A tranquil harborside retreat a stone’s-throw away on idyllic Shelter Island

Accommodations
Individually appointed, fully furnished one- and two-bedroom suites and villas, each with private balcony or porch, ideal for both weekend and long-term stays
Property

Lovingly maintained seven-acre estate, teeming with wildlife, on a bluff overlooking Dering Harbor and the North Fork panorama

Property

Lovingly maintained seven-acre estate, teeming with wildlife, on a bluff overlooking Dering Harbor and the North Fork panorama

Amenities

Access to gym and fitness studio, temperature-controlled outdoor swimming pool and lounge deck, and outdoor hardcourt tennis courts

Location

Minutes from the North Ferry, steps from Shelter Island Heights and downtown thoroughfare, and a short jog to all island attractions — all under three hours, by train, bus, or car, from New York City

Location

Minutes from the North Ferry, steps from Shelter Island Heights and downtown thoroughfare, and a short jog to all island attractions — all under three hours, by train, bus, or car, from New York City

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Fitness & Wellness

The Dering Harbor Inn clubhouse — a jewel of the property’s midcentury architectural heritage — is home to Shelter Island Yoga & Fitness and Moussa Drame Tennis. Open to islanders and guests of the inn alike, SIY&F offers regular yoga, pilates, spin, and STX classes with professional instructors; tennis clinics; full gym outfitted with free weights and machines; and fresh-juice and coffee bar.

For runners, cyclists, hikers, and outdoor enthusiasts of all stripes, the inn is a threshold to the island’s miles of scenic rolling terrain, pristine beaches, and the cherished Mashomack Nature Preserve.