The mustard yellow Twin Gables (73 Tinker St., 845/679-9479, www.twingableswoodstockny.com, $89–160) has functioned as a homey, affordable guesthouse since the 1940s and claims to be the oldest house in Woodstock. Some of the nine guest rooms share baths.
Also downtown, you’ll find the attractive Woodstock Inn on the Millstream (38 Tannery Brook Rd., 845/679-8211, www.woodstock-inn-ny.com, $129–245 d with breakfast, two-night minimum on summer weekends), an upscale motel with a variety of room setups. The inn is in walking distance of Mill Stream natural brook and swimming hole, a local favorite cool-down spot in the summer.
Elegance and convenience mingle in the Wild Rose Inn (66 Rock City Rd., 845/679-8783, www.thewildroseinn.com, $150–250) just a block from the village green. This B&B offers cushy furnishings, private whirlpool bathtubs, and private entrances to all rooms, with a friendly owner well-versed in all things local.
Built as the home of Woodstock artist Jo Cantine, the elegant, hide-away Woodstock Country Inn (27 Cooper Lake Rd., 845/679-9380, www.woodstockcountryinn.com, $185–300) offers four guest rooms filled with light and antiques. There is also an outdoor pool and great mountain views.
© Avalon Travel and Sascha Zuger from Moon New York State, 5th Edition