Five miles north of Rhinebeck  is Red Hook, a small, low-key village filled with a surprising number of restaurants, inns and B&Bs, and historic buildings, such as the Octagonal House (7444 S. Broadway), which now houses the Red Hook Library.
Anchoring the village is the handsome Federal-style Red Hook Inn (7460 S. Broadway, 845/758-8445, $180–275 d), sporting a wide front porch. Inside are five spacious guest rooms and a suite, a restaurant serving fresh regional fare (average entrée $16), and a cozy tavern complete with a fireplace and mahogany bar.
Within walking distance of downtown is the striking, blue Grand Dutchess Bed and Breakfast (7571 Old Post Rd., 845/758-5818, www.granddutchess.com , $155–195 d), a Victorian Italianate mansion offering six light-filled guest rooms. All have private baths and air-conditioning, and antiques are everywhere.
A good spot for breakfast, lunch, or a simple dinner is the wonderful old Village Diner (39 N. Broadway, 845/758-6232). Built in 1927, the art deco eatery is still family-owned and operated. Try the homemade doughnuts, soups, and egg creams.
The Hudson Valley  region in general has been a supplier of cut flowers since Victorian times, and Dutchess County in particular was once the violet and anemone capital of the world. One of the oldest nurseries still around is F. W. Battenfeld & Sons (Rte. 199, 845/758-8018, www.anemones.com ), just outside Red Hook. The best time to visit is October–May, when the anemones are in bloom.
Also of note near Red Hook is the large, family-owned Greig Farm (223 Pitcher Ln., just west of Rte. 9, 845/758-1234, www.greigfarm.com , daily July–Oct.), where you can pick your own apples, pumpkins, peaches, and berries.