Old Town Winchester, VA
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. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Shenandoah Valley Discovery Museum
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
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
George Washington's Office
You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor 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 savor the top-notch restaurants.
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
$118 nightly
The price is $134 total per night from Aug 31 to Sep 1
$134 total
Aug 31 - Sep 1
Total with taxes and fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,001 reviews)
"Hotel has a walking mall right around the corner. Beds and pillows are always comfortable. Has nightly entertainment on weekends onsite at the Bar/Restaurant."
Reviewed on Aug 19, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
$103 nightly
The price is $112 total per night from Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total with taxes and fees
Stay at this 3-star 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! (2,129 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"
Reviewed on Aug 19, 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
$85 nightly
The price is $92 total per night from Aug 31 to Sep 1
$92 total
Aug 31 - Sep 1
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"Bed comfort"
Reviewed on Aug 12, 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Sep 15 to Sep 16
$86 total
Sep 15 - Sep 16
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! (1,324 reviews)
"easy to get to, close to where I needed to be."
Reviewed on Aug 19, 2025
SpringHill Suites by Marriott Winchester
280 MARKET STREET, Winchester, VA
$116 nightly
The price is $126 total per night from Sep 1 to Sep 2
$126 total
Sep 1 - Sep 2
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! (694 reviews)
"Fabulous all around. Comfortable beds, great breakfast, super clean and great staff. Great stay!"
Reviewed on Aug 20, 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
$71 nightly
The price is $79 total per night from Sep 1 to Sep 2
$79 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,000 reviews)
A night in Virginia
"Room was comfortable. The breakfast was decent. The Mexican restaurant attached is AMAZING. No conditioner and body wash was super low. I’m sure I could have gotten more if I asked but it was not a big deal. I did ask for more towels and they were quickly accommodating."
Reviewed on Aug 19, 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 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 Winchester Little Theater.
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