Located right on the village green, Laurence S. Rockefeller's Woodstock Inn & Resort (from $235 per person, with meals) is a great launching pad for exploring Woodstock, a town as walkable as Manhattan. The resort conceals an eighteen-hole golf course, tennis center, 41,000-square-foot fitness center, and small spa behind its Colonial façade.
Set in an 1890 Victorian mansion, the Jackson House Inn (from $195) distinguishes itself from the other country-B&B experiences with period antiques and a sunset cocktail hour, as well as an excellent restaurant.
The new Lauren Inn (from $233 on weekends) melds the traditional charms of a ten-room B&B with lavish bathrooms, flat-screen TVs, and iPod docks.
Former home to Sinclair Lewis and Dorothy Parker, Twin Farms (from $1,050) is arguably the most luxurious resort in the Northeast, with ten house-size cottages, ten additional suites, and everything from private ski trails to traditional Japanese baths. Book Orchard Cottage for the most stylish room.