Hotels in Winchester

Tucked within the pastoral Shenandoah Valley and surrounded by apple orchards, Winchester is the “Apple Capital of Virginia”. With a quaint Old Town centre and variety of historic walking tours, it’s easy to fall back into yesteryear elegance at Winchester.

Things to do in Winchester

Discover the graceful hospitality of Winchester in the Old Town area and its Loudoun Street Pedestrian Mall lined with eateries, antiques and locally-owned shops. Take guided tours to see period furniture and decor at Abram’s Delight museum as well as Civil War relics at Stonewall Jackson’s Headquarters.

The arts take centre stage at venues, such as Bright Box Theatre and Magic Lantern Theatre, which present drama productions, live music, comedy and entertainment. After the show, walk through the historic district for craft beer and wine tasting.

Explore the country’s agricultural roots at the region's family-owned farms and produce stands, such as Freight Station Farmers Market. You can go apple picking, sample freshly-pressed apple cider and take a hay-cart ride.

At Valerie Hill Vineyard and Winery, you can roam through spellbinding architecture from the early 1800s while enjoying live music and small-bite food pairings and wine tasting. As the weather turns colder, cuddle up for Firepit Fridays or sign up for a “History and Hauntings” dinner. Veramar Vineyard plays host to outdoor movie nights, Friday “wine downs” and special culinary events.

Getting around Winchester

The Old Town area is pedestrian-friendly and the Winchester public transit system operates bus routes. Taxis are available or you can rent a car at nearby Winchester Regional Airport. Washington Dulles Airport is about one hour away by car.