Winchester Inn, Restaurant & Wine Bar

Ashland contains many historic buildings, among them the Winchester Inn, Restaurant & Wine Bar built in 1886 as a private home, and at one time used as a hospital. Its quiet but central location, two blocks south of the Shakespeare Festival grounds and one block above Main Street, makes it perfect for coming home to relax between shopping excursions or attending one of the many theatrical performances. Guestrooms are found in two historic Victorian and two additional buildings, all cleverly woven together with walkways and gardens. Bedrooms all have a Victorian flair and come in a large variety of shapes and sizes—some can accommodate an extra bed and there are several suites and apartments suitable for families. Bathrooms in the more deluxe guestrooms have both showers and Jacuzzi or whirlpool tubs. We loved our luxurious accommodation in the Robert Gordon Suite with its spacious sitting room, king bed, and whirlpool tub. Breakfast—fruit, juice, freshly baked pastries, and a choice of three cooked entrees—is served on the spacious garden patio in summer, in the dining room in winter. Be sure to include dinner at the inn in your Ashland dining plans.