The famed Beekman Arms (6387 Mill St., 845/876-7077, www.beekmandelamaterinn.com) is an inn that has expanded in recent years to include a cluster of about 10 small buildings. Rooms in the historic main building ($140–150 d) have plenty of atmosphere but are small; those in the handsome, American Gothic
Delamater Inn ($100–250 d), designed by Alexander Jackson Davis, are the most splendid and popular. Also at Delamater are six guesthouses perfect for families. Rooms in the other buildings cost $100–300 d.

B&B fans will find many good choices in the area. In the heart of town is the Gothic Victorian Gables at Rhinebeck (6358 Mill St., 845/876-7577, $150–225 d). Once owned by two eccentric sisters who shared the house with a huge doll collection, the home now offers three recently renovated guest rooms and an inviting porch. A complimentary afternoon tea with lemonade and scones is served.

The Rhinecliff (4 Grinnell St., 845/867-0590, www.therhinecliff.com, $160–190), an 1854 renovated rooming house offers all the modern luxury amenities you could need, including Wi-Fi, whirlpool tubs, and views of the Hudson from every room. This boutique country hotel has been touted for its authentic sense of place and features a restaurant and bar worthy of a pop in.

On the outskirts of town, surrounded by fields and woodlands, is the delightful Whistle Wood Farm (52 Pells Rd., off Rte. 308, 845/876-6838, www.whistlewood.com, $120–325 d). Both a working horse farm and a friendly B&B, the Whistle Wood boasts a Jacuzzi, decks overlooking the corral and fields of wildflowers, and plenty of in-room amenities. Stay in the main house or in the Carriage House, divided into two suites.

Motels in town include the tiny, eight-room Rhinebeck Motel (117 Rte. 9, 845/876-5900, $99–115 d) and the family-owned Rhinebeck Village Inn (6 Rte. 9, 845/876-7000, $80–98 d). Both are clean and friendly.