Cranwell Resort & Golf Course 55 Lee Rd., Lenox; 413/637-
1364, fax 413/637-0571; doubles from $89 in winter, $199 in summer. Pretend you're Gatsby at this old-style resort housed in 1890's buildings on 380 acres, with an 18-hole golf course, tennis courts, and a heated pool.
Apple Tree Inn & Restaurant 10 Richmond Mountain Rd., Lenox; 413/637-1477, fax 413/637-2528; doubles from $55 in winter, $155 in summer. Perched on a 22-acre hilltop estate across the road from Tanglewood, this 1885 house was Alice's Restaurant (made famous by Arlo Guthrie) until 1979. On the grounds are a pool, clay tennis courts, and a network of walking trails.
Blantyre 16 Blantyre Rd., Lenox; 413/637-3556, fax 413/637-4282; doubles from $295; open early May through early November. A 1902 Tudor mansion—the Berkshires' only Relais & Châteaux property—offering surprisingly friendly service and aristocratic style, with tennis, swimming, and croquet.
Red Lion Inn 30 Main St., Stockbridge; 413/298-5545, fax 413/298-5130; doubles from $100 in winter, $175 in summer. Rambling inn with a lovely veranda, a cozy lobby, and canopy or four-poster beds in most of the 110 rooms.
Williamsville Inn Rte. 41, West Stockbridge; 413/274-6118, fax 413/274-3539; doubles from $120 in winter, $140 in summer. A 1797 farmhouse converted to an inn in 1952. The secluded 10-acre property holds a beautiful sculpture garden (open in summer), pool, tree swing, and tennis courts. A favorite for weddings.
Canyon Ranch in the Berkshires 165 Kemble St., Lenox; 800/742-9000 or 413/637-4100, fax 413/637-0057; doubles from $1,204 per person for a three-night minimum stay. This outpost of Tucson's renowned health-and-fitness resort opened in 1989 and provides all the treatments and services you'd expect. At the heart of the 120-acre estate is Bellefontaine, a grand 1897 "cottage" modeled after Versailles's Petit Trianon.
Kripalu Center for Yoga & Health Route 183, Stockbridge; 800/967-3577 or 413/448-3400, fax 413/448-3384; dormitory beds from $77, private doubles from $118. The Retreat & Renewal package, included in all room rates, offers workshops in yoga, breathing, meditation, and DansKinetics. Set on a hill above the Stockbridge Bowl. Day passes available
Bistro Zinc 56 Church St.; 413/637-8800; dinner for two $70. Barely a year old, this stylish restaurant is straight out of SoHo, and draws an appropriately chic crowd with its gorgeous bar and excellent French bistro food.
Church Street Café 65 Church St.; 413/637-2745; dinner for two $60. A Lenox favorite, serving eclectic American food in several softly lit dining rooms and, in summer, on a shaded terrace. Unfortunately, the quality of the entrées has gone down a bit lately; make a meal of the excellent appetizers.
Spigalina 80 Main St.; 413/637-4455; dinner for two $60. Mediterranean cuisine served in a white clapboard house with a porch facing Main Street. Popular among Lenox's well-to-do for pre-Tanglewood dinners.
Baba Louie's Woodfired Pizza Restaurant 286 Main St.; 413/528-8100; dinner for two $25. Wood-fired pies with wholesome all-organic toppings. Virtuous as all get-out.
Bizen Japanese Restaurant & Sushi Bar 17 Railroad St.; 413/528-4343; dinner for two $75. Spectacular sushi and sashimi (the fresh fish is driven in daily from New York) served on chef Michael Marcus's own hand-crafted dinnerware. Prices are high but portions generous.
Union Bar & Grill 293 Main St.; 413/528-6228; dinner for two $50. Trendy hot spot with loft ceilings and sleek wood-and-aluminum interior, drawing an equal number of young hipsters and families (kids like the noise level). Very good New American food with French and Asian accents.
Lion's Den Main St.; 413/298-1654. Anglophiliac alert: The coziest pub in the county, in the cellar of the Red Lion Inn. Live music most nights—some of it intolerable, but hey, you can't win 'em all. Popular with tourists, always packed.
La Bruschetta Ristorante 1 Harris St.; 413/232-7141; dinner for two $60. Friendly and casual, with one of the longest wine lists in the Berkshires. Try the splendid bruschettas and risottos, and the osso buco.
Truc Orient Express 3 Harris St.; 413/232-4204; dinner for two $40. If you thought great Vietnamese food couldn't be found in a Berkshires hamlet, think again. This two-decade-old favorite, housed in a former warehouse, is still going strong.
Williamsville Inn Rte. 41; 413/274-6118; dinner for two $60. Elegant and eclectic New American and classic country dishes served in old-fashioned dining rooms.
Jack's Grill Main St.; 413/274-1000. A delightfully quirky place serving comfort food (pot roast, mac and cheese) in a former hardware shop outfitted with kitschy memorabilia and a model train. Great for kids, obviously.
Cactus Café 54 Main St.; 413/243-4300; dinner for two $50. The most authentic Mexican food around, which admittedly isn't saying much—but it really is excellent. The large tin-ceilinged dining room has a funky cantina theme.
Mezze 84 Water St.; 413/458-0123; dinner for two $60. The latest addition to Williamstown's refined dining scene, offering creative Mediterranean food. A post-show hangout for cast members from the Williamstown Theatre Festival.