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
The price is NT$3,840 per night from Sep 28 to Sep 29
NT$3,840
NT$4,351 total
Sep 28 - Sep 29
includes taxes & 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! (1,000 reviews)
"Perfect location to visit for business or pleasure!"
Reviewed on 2025/9/7
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is NT$3,284 per night from Sep 17 to Sep 18
NT$3,284
NT$3,573 total
Sep 17 - Sep 18
includes taxes & 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! (2,138 reviews)
"We mistakenly left a watch in the room after we checked out, and the front-desk person let us go back to check the room about an hour later. Fortunately, the watch was found!"
Reviewed on 2025/9/9
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NT$2,668 per night from Sep 15 to Sep 16
NT$2,668
NT$2,994 total
Sep 15 - Sep 16
includes taxes & 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! (1,000 reviews)
"Very clean & comfortable. Staff was very helpful & pleasant."
Reviewed on 2025/9/8
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
The price is NT$2,092 per night from Sep 11 to Sep 12
NT$2,092
NT$2,276 total
Sep 11 - Sep 12
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,090 reviews)
"Staff is very accommodating and efficient. Room was clean, bed very comfortable. Housekeeper does a fantastic job. Breakfast is very good. Hotel is pet friendly which we appreciate."
Reviewed on 2025/9/7
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
The price is NT$2,557 per night from Sep 21 to Sep 22
NT$2,557
NT$2,782 total
Sep 21 - Sep 22
includes taxes & 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! (1,330 reviews)
"Beautiful hotel staff was very nice and helpful. Only thing I didn't care for was that out room was next to the elevator shaft so we could hear the elevator anytime some used it but the front desk staff told us they were sorry that we may hear it and if it became a issue they would move us."
Reviewed on 2025/9/8
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
The price is NT$2,165 per night from Sep 17 to Sep 18
NT$2,165
NT$2,410 total
Sep 17 - Sep 18
includes taxes & 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! (1,002 reviews)
"Spacious clean room. Excellent breakfast especially the pancake machine."
Reviewed on 2025/9/5
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 Winchester Little Theater.
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