Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Popular places to visit
Museum of the Shenandoah Valley
5/5(19 reviews)
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Jim Barnett Park
4/5(1 review)
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Shenandoah Valley Discovery Museum
4.5/5(11 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Bright Box Theater
4.5/5(4 reviews)
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Handley Regional Library
5/5(2 reviews)
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
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 savor the top-notch restaurants.
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$127 nightly
The price is $143 total per night from Feb 5 to Feb 6
$143 total
Feb 5 - Feb 6
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,001 reviews)
Pleasant Relaxing
Reviewed on Jan 23, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$92 nightly
The price is $100 total per night from Jan 29 to Jan 30
$100 total
Jan 29 - Jan 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,251 reviews)
Very Friendly staff and clean rooms!
Reviewed on Jan 25, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
$85 nightly
The price is $92 total per night from Feb 2 to Feb 3
$92 total
Feb 2 - Feb 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,441 reviews)
Perfect for a single night, relatively clean, very friendly staff and decent breakfast.
Reviewed on Jan 18, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Jan 29 to Jan 30
$76 total
Jan 29 - Jan 30
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,071 reviews)
Good value, clean, comfortable bed. Bathroom fan was connected to light so couldnt leave light on in the bathroom as a night light. Fan was loud. All in all..id stay there again when traveling.
Reviewed on Jan 20, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$82 nightly
The price is $89 total per night from Feb 15 to Feb 16
$89 total
Feb 15 - Feb 16
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,000 reviews)
The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ...
Reviewed on Jan 18, 2026
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
$98 nightly
The price is $106 total per night from Feb 22 to Feb 23
$106 total
Feb 22 - Feb 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,102 reviews)
Staff was very friendly and room was great!
Reviewed on Jan 27, 2026
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.
Check Old Town Winchester hotel availability
Other neighborhoods 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, VA
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