Another well-priced property for wooing in the Wine Country, this is right on the trendy main square of Healdsburg. The 12 guest rooms in this 1901 building offer high ceilings and tall windows, and some sport balconies, exposed brick walls and/or period details like claw-foot tubs and crown molding, creating a sense of spaciousness and intimacy at the same time. As a member of the Four Sisters Inns collection, rates include a chef-made breakfast for two, delivered to your room, as well as a “mini-picnic” bag of wine, cheese and homemade cookies.