Though closed to the public from January through March, the classic Ram’s Head Inn, located in the heart of Shelter Island, still welcomes private winter guests.
For a special rate of $1,700, the inn offers exclusive private weekend bookings. Guests who reserve a winter weekend receive the keys and sole access to the inn’s charming rooms, making it an ideal setting for family gatherings or groups of friends seeking a peaceful seasonal retreat.
The second floor of the spacious property features 17 unique guestrooms designed to reflect the history and waterfront charm of the inn while providing comfortable, understated luxury. Accommodations include five rooms with private baths, four bedrooms sharing baths, and four two-bedroom suites, each arranged to suit different group sizes and preferences.
From April through December, Ram’s Head Inn comes alive with outdoor activities and waterfront recreation. The property offers a multiuse tennis court that doubles as a basketball court, a private 800-foot beach, hammocks and Adirondack chairs for lounging, plus access to a fleet of sailboats, paddleboards, kayaks and swimming moorings.
The inn also hosts a celebrated farm-to-table restaurant led by Chef Joe Smith. The kitchen focuses on a seasonal menu featuring fresh local produce, game and seafood, reflecting the rhythms of the region through the end of the year.