Thoughtfully restored with original beams, wide-board floors, five fireplaces, and a hillside sauna cottage, the 12-acre property sits in Pawling, about 90 minutes from New York City.

Listed in the MICHELIN Guide, the heritage-designated Merrill House in Picton offers 14 guest suites, restaurant and bar infrastructure with a commercial kitchen, and a climate-controlled wine cellar in one of Ontario’s best-known wine-country regions.

Located in the Catskill Mountains roughly two hours from New York City, Woodstock is one of the Hudson Valley’s longest-standing artist communities. Built in 1925 by local artist Paul Arndt, Library Lane is within walking distance of the village center.