There are no bad views from the Shinn Estate Farmhouse (from $275), the only on-vineyard inn on the North Fork. Enjoy a bottle of Shinn’s rosé in the Northfield Room, with its sunset view of the Long Island Sound. Hard-core oenophiles should sign up for a Wine Asylum Weekend ($1,000 per couple): three days of working in the vineyards, tasting wines, and refueling with meals cooked by co-owner David Page, who also owns New York’s Home with wife Barbara Shinn.
The year-old North Fork Table & Inn ($250), houses four elegant rooms in a white-columned Colonial on Route 25 in Southold. Meals are served in a pretty, pale-blue dining room, where a nightly changing menu features dishes like crispy-skinned black sea bass in a carrot-ginger broth, and, of course, a good local wine list.
At the Red Barn Bed & Breakfast (from $175) in Jamesport, owners and Slow Food members Linda and Jim Slezak serve lemonade with homemade cookies on the wraparound front porch and a three-course breakfast using mostly local, organic ingredients. Take public transportation out to the East End, and they’ll pick you up at the station—and knock 10 percent off your room.
Jamesport resident Jeff Hallock recently completed a four-year restoration on the once dilapidated, now immaculate former sea captain’s home, the Jedediah Hawkins House (from $325). The Key-lime-colored mansion, originally built in 1863, has six creatively decorated rooms, but the top-floor Belvedere Suite is the best, with its 360-degree views, and telescope for stargazing.