Vivid, Authentic, Historic
“Winchester: Where history, charm, and culture beautifully blend.”
Stay & Play Near James Charles Winery
“Explore the rich history and natural beauty of the Shenandoah Valley, with a variety of activities, charming lodging options, and delicious dining experiences all just a short drive away from James Charles Winery. Whether you’re looking for adventure, relaxation, or a taste of local culture, there’s something for everyone to enjoy!”
Nearby Activities
- Museum of the Shenandoah Valley – Explore beautiful gardens, galleries, and historic homes.
- Skyline Drive – Scenic drives through Shenandoah National Park.
- Apple Blossom Mall – Enjoy shopping and entertainment options.
- Old Town Winchester – Discover dining, boutiques, and historic landmarks.
- Abram’s Delight Museum – Winchester’s oldest home turned museum.
- Rocking S Ranch – Guided horseback trail rides.
- Shenandoah Valley Discovery Museum – Interactive fun for families and kids.
- Belle Grove Plantation – A historic home and events venue.
- George Washington’s Office Museum – A peek into Winchester’s rich history.
- Winchester Ciderworks – Craft cider tastings.
- Veramar Vineyard – Experience award-winning wines and stunning vineyard views in the heart of the Shenandoah Valley.
- Valerie Hill Vineyard and Winery – A charming, historic winery offering a welcoming atmosphere and handcrafted wines.
Lodging Options
- The George Washington Hotel – Historic charm in Old Town Winchester.
- Hampton Inn Winchester – Comfortable and convenient lodging.
- SpringHill Suites Winchester – Modern and spacious accommodations.
- The Inn at Vaucluse Spring – Elegant bed-and-breakfast experience.
- La Quinta by Wyndham Winchester – Family and pet-friendly.
- L’Auberge Provencale Bed and Breakfast – French-inspired luxury.
- Holiday Inn Winchester SE-Historic Gateway – Convenient for families.
- Courtyard by Marriott Winchester Medical Center – Business and leisure-friendly.
- The Country Inn & Suites by Radisson – Comfortable and family-oriented.
- Historic Rosemont Manor – A boutique historic estate.
Restaurants
- Village Square Restaurant – Upscale dining in Old Town Winchester.
- Violino Ristorante Italiano – Authentic Italian cuisine.
- The Butcher Station – Farm-to-table dining experience.
- Union Jack Pub & Restaurant – British-inspired fare.
- Roma Old Town Wood-Fired Pizzeria – Delicious wood-fired pizzas.
- 50/50 Taphouse – Great food and local craft beers.
- Piccadilly Public House – Pub-style dining with a historic ambiance.
- Thai Winchester – Fresh and flavorful Thai dishes.
- Awabi Sushi Bar – Sushi and Japanese delicacies.
- Daily Grind – Cozy café for coffee and light bites.
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Learn More
To learn more, please call, email or fill out the contact form below – we will respond as quickly as possible.