Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Popular places to visit
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Museum of the Shenandoah Valley
5/5(1 review)
You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.
Shenandoah Valley Discovery Museum
4/5(1 review)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Bright Box Theater
Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
Old Court House Civil War Museum
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
George Washington's Office
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is 3.340.014 ₫ per night from 8 Dec to 9 Dec
3.340.014 ₫
3.784.382 ₫ total
8 Dec - 9 Dec
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.2/10 Wonderful! (1,003 reviews)
The breakfast was very good. The menu had a lot of options. It came to our table nice and hot! I loved the waffle with Lemon ricotta, syrup and butter. Our waitress always knew when to fill my coffee to keep it warm! Everything was very clean and neatly set up. The waitresses were also cheerful and ...
Reviewed on 20 Nov 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is 2.465.969 ₫ per night from 17 Dec to 18 Dec
2.465.969 ₫
2.683.027 ₫ total
17 Dec - 18 Dec
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,227 reviews)
Safe parking. Pet friendly
Reviewed on 22 Nov 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is 1.793.432 ₫ per night from 1 Dec to 2 Dec
1.793.432 ₫
1.951.254 ₫ total
1 Dec - 2 Dec
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.4/10 Very Good! (1,093 reviews)
Clean and comfortable.
Reviewed on 23 Nov 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is 1.898.928 ₫ per night from 15 Dec to 16 Dec
1.898.928 ₫
2.066.034 ₫ total
15 Dec - 16 Dec
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,371 reviews)
Room and public areas were very clean and well taken care of.
Reviewed on 26 Nov 2025
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is 2.443.366 ₫ per night from 3 Dec to 4 Dec
2.443.366 ₫
2.658.381 ₫ total
3 Dec - 4 Dec
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,057 reviews)
The staff was courteous, and the room was spotless. The location was perfect for us.
Reviewed on 23 Nov 2025
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
The price is 2.227.021 ₫ per night from 15 Dec to 16 Dec
2.227.021 ₫
2.422.998 ₫ total
15 Dec - 16 Dec
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,007 reviews)
Staff at front desk were courteous, location was good, hotel was cleanish. Our bathroom had mold on entire ceiling and general damp smell. Found stray sock (not ours) under bed.
Reviewed on 22 Nov 2025
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.
Other neighbourhoods around Old Town Winchester
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
Old Town Winchester Travel Guide
- Places of interest
- Hotels in Old Town Winchester by Star Rating
- Choose Your Old Town Winchester Hotel Style
- Hotels in top Winchester neighborhoods
- Search Old Town Winchester Hotel Brands
- Handley Regional Library
- Old Court House Civil War Museum
- Hollywood Casino at Charles Town Races
- Shenandoah University
- George Washington National Forest
- Shenandoah River
- Apple Blossom Mall
- Bluemont Vineyard
- Museum of the Shenandoah Valley
- Jefferson County Courthouse
- Sky Meadows State Park
- Lost River
- Belle Grove Plantation
- Charles Town Library
Choose Your Old Town Winchester Hotel Style
- Beach Resorts & Hotels in Old Town Winchester
- Business Hotels in Old Town Winchester
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- Family-Friendly Hotels in Old Town Winchester
- Golf Hotels in Old Town Winchester
- Hotels near Museums in Old Town Winchester
- Hotels with Air Conditioning in Old Town Winchester
- Hotels with Breakfast in Old Town Winchester
- Hotels with Entertainment in Old Town Winchester
- Hotels with Gym in Old Town Winchester
- Hotels with Hot Tubs in Old Town Winchester
- Hotels with Indoor Pools in Old Town Winchester
- Hotels with Pool in Old Town Winchester
- Hotels with Room Service in Old Town Winchester
- Hotels with Wifi in Old Town Winchester
- Hotels with a Bar in Old Town Winchester
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- Sports Hotels in Old Town Winchester
- Wedding Hotels in Old Town Winchester
