39.1867-78.16672Handley Library (Handley Regional Library), 100 W. Piccadilly Street (Corner of Rt. 7 and Rt. 11), ☏ +1 540 662-9041. 10-8 (M-W) and 10-5 (Th-S). A library ornately designed in the Beaux Arts style that opened to the public in 1913. Includes the Nancy Larrick Children's Room, the Middle Kingdom for teens, Information services and the Stewart Bell, Jr. Archives.
39.184893-78.1681453Tomb of Lord Fairfax. The final resting place of Thomas Fairfax, 6th Lord Fairfax of Cameron, the proprietor of all of Northern Virginia during colonial times. The tomb is on the grounds of the historic Christ Episcopal Church. (updated Sep 2019)
39.1839-78.16444Shenandoah Valley Civil War Museum (Old Frederick County Courthouse). Civil war museum displaying local artifacts such as insignia and firearms, in a former courthouse built in 1940. (updated Sep 2019)
Snow White Grill, 159 N. Loudoun St (Along the central pedestrian walkway), ☏ +1 540 662-5955. A cheap and greasy local favorite that serves delicious mini-burgers, birch beer, and milkshakes. Eat inside or out.
Cork Street Tavern, 8 West Cork Street (In old town Winchester), ☏ +1 540 667-3777. American food including ribs. Outdoor seating during summer.
[dead link]Tater Hill Tavern, 618 South Loudoun Street (inside the Nancy Shepherd House Inn), ☏ +1 540-247-5073. by appointment only. This amazing ancient tavern ale and wine room is inside the Nancy Shepherd House Inn. If you like historic early taverns, this one is a must see while visiting Winchester, but you must be an overnight guest of the Inn for the privilege...or if you are not an overnight guest, you might try your luck and call to see if the innkeepers will invite you in anyway. It's worth a try.
Old Waterstreet Inn - 19th century house. Some rooms with fireplace; breakfast and cocktails included. $120-155.
George Washington Hotel - Luxury suites with fireplaces and whirlpool tubs. Spa and pool.
Long Hill Bed & Breakfast. #1 inn in the South. Custom 10,000 sq.ft. house on 20 A. Savor an award winning family style gourmet breakfast. View birds & wildlife. Great getaway; vacation anchor. Shoot pool; work puzzles; Good food, good rest; feel like family when you leave.
Nancy Shepherd House Inn Bed and Breakfast, 618 South Loudoun Street Winchester VA 22601 (right downtown on Winchester's main street), ☏ +1 540-247-5073. Great value with a fantastic breakfast. Very interesting historic inn right downtown with excellent restaurants, shops, pubs, coffee houses, and museums all around. Four extremely comfortable & cozy bedrooms, two with fireplaces. $79 - $139.