The mustard yellow Twin Gables (73 Tinker St., 845/679-9479, www.twingableswoodstockny.com [1], $89–160) has functioned as a homey, affordable guesthouse since the 1940s and claims to be the oldest house in Woodstock [2]. 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 [3], $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 [4], $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 [2] artist Jo Cantine, the elegant, hide-away Woodstock Country Inn (27 Cooper Lake Rd., 845/679-9380, www.woodstockcountryinn.com [5], $185–300) offers four guest rooms filled with light and antiques. There is also an outdoor pool and great mountain views.
Links:
[1] http://www.twingableswoodstockny.com
[2] http://www.moon.com/destinations/new-york-state/the-hudson-valley/mid-hudson-valley/the-catskills/woodstock
[3] http://www.woodstock-inn-ny.com
[4] http://www.thewildroseinn.com
[5] http://www.woodstockcountryinn.com