Plan your trip

A white neoclassical building with columns, an American flag, and a clock tower.

Find Hotels with Bar in Winchester, VA from CA $86

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Sign in

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, December 14–15, 2026

    View in a map

    Our top choices for Winchester hotels with a bar

    1. The George Washington Hotel, A Wyndham Grand Hotel

    A hotel room with a large window, a chandelier, and a carpeted floor.

    2. Holiday Inn Winchester Se-Historic Gateway by IHG

    A Holiday Inn Express hotel with a covered entrance, multiple floors, and flags.

    3. Courtyard by Marriott Winchester

    A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

    4. Hilton Garden Inn Winchester

    A modern interior with a geometric ceiling design, recessed lighting, and hanging spherical light fixtures.

    5. Ramada by Wyndham Strasburg/Shenandoah Valley

    A modern hotel lobby with a clear exit sign, a reception desk, and a seating area with red chairs.

    6. DoubleTree by Hilton Front Royal Blue Ridge Shadows

    A restaurant interior with a bar area, seating, and artwork on the walls.

    7. Econo Lodge Inn & Suites Middletown - Winchester South

    A hotel room with a neatly made bed, a bedside lamp, and a window with curtains.

    8. L'Auberge Provencale Inn & Restaurant

    A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

    9. Baymont by Wyndham Front Royal Near Shenandoah National Park

    A breakfast station with coffee dispensers, hot water, and a bowl of silverware.

    10. Glen Gordon Manor

    A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

    View all properties

    Top Winchester Hotel Reviews

    Hotel Burg

    A hotel with a brick facade, multiple windows, and a well-lit entrance.

    The George Washington Hotel, A Wyndham Grand Hotel

    A hotel room with a large window, a chandelier, and a carpeted floor.

    Hilton Garden Inn Martinsburg

    A room with two sofas facing a large window, a small round table, and a potted plant.

    L'Auberge Provencale Inn & Restaurant

    A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

    Salamander Middleburg

    A large, two-story house with a central entrance, multiple chimneys, and a well-maintained lawn with a pathway leading to the entrance.

    Courtyard by Marriott Winchester

    A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

    Hilton Garden Inn Winchester

    A modern interior with a geometric ceiling design, recessed lighting, and hanging spherical light fixtures.

    DoubleTree by Hilton Front Royal Blue Ridge Shadows

    A restaurant interior with a bar area, seating, and artwork on the walls.

    Homewood Suites by Hilton Leesburg

    An outdoor patio area with a wooden pergola, a grill, and seating.

    Frequently Asked Questions

    Searching for hotels with bars in Winchester?

    Winchester features 75 properties to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Bright Box Theater and Shenandoah Valley Discovery Museum.

    What are the best hotels with bars in Winchester?

    Here's some of the top Winchester accommodations with bars: The George Washington Hotel, A Wyndham Grand Hotel: Hotel with 2 restaurants. Enjoy the bar, free WiFi, and full-service spa. Holiday Inn Winchester Se-Historic Gateway by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Courtyard by Marriott Winchester: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Winchester: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.

    How many hotels with bars can I expect to find in Winchester?

    Expedia has 5 hotels with a bar in Winchester.

    What is there to do in Winchester?

    Consider a visit to Bright Box Theater, Shenandoah Valley Discovery Museum, and Patsy Cline Historic House, and then find a cozy spot for a nightcap. Other places to see include Museum of the Shenandoah Valley and Apple Blossom Mall. Winchester is popular for its array of shops and top-notch restaurants.

    When is the best time to visit Winchester?

    Visiting local bars in Winchester is more fun when you know what the weather holds. These rainfall averages and temperatures can help you decide the best time for bar hopping. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.

    How can I get to Winchester and around the area?

    Here are some of your transportation options in and around Winchester: Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center. You can also search for flights into Washington Dulles Intl. Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

    Explore a world of travel with Expedia