Ask for the Magnolia Room with a deck overlooking the Hudson at Botsford Briar (from $145), a restored, five-bedroom Queen Anne Victorian home. Metal sculptures and vibrant quilts created by artists turned B&B owners Shirley Botsford and Charles Fincham are displayed throughout.
Call a month in advance to reserve one of the three guest rooms at Mt. Beacon Bed and Breakfast (from $165), a three-story mansion outfitted with antique four-poster beds, claw-foot tubs, and wood-burning fireplaces. In the morning, walk the surrounding hiking trails ranging from one to eight miles.
Purchase paintings by Hudson Valley landscape artist Roberta Griffin and watercolorist M.E. Whitehill (from $300) at Swann Inn, a restored 1866 home decorated and run by Parsons-trained fashion designer Darlene Swann Caplan (from $157).