Book a weekend stay three months in advance at the nine-room Rhinecliff Hotel (from $180), a former live-music venue turned Victorian hotel. All rooms include private balconies with views of the Hudson River, and the hotel is an easy walk to the waterfront.
Sip some complimentary sherry from the decanter in your room at Beekman Arms (from $125), the oldest continuously operated hotel in the U.S., founded in 1766. The no-frills country-style spot is steeped in past presidential history: George Washington lodged in room 21 during the Revolutionary War, and the Clintons hosted Chelsea’s rehearsal dinner here in July.
Lounge in a white-tiled Jacuzzi in the Ivy Room at Veranda House (from $180), a floral-themed B&B outfitted with lace curtains and nineteenth-century antiques. Owner Yvonne Sarn creates breakfast specialties like ratatouille and goat-cheese crêpes and blueberry custard casserole.