Winchester Historic District

Winchester

Winchester Historic District
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Popular places to visit

Handley Regional Library

Handley Regional Library

5/5(1 review)

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.

Handley Regional Library
Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(1 review)

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.

Museum of the Shenandoah Valley

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.

Shenandoah Valley Discovery Museum

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.

Bright Box Theater

Winchester Little Theater

Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.

Winchester Little Theater

Stonewall Jackson's Headquarters

Learn about the local history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Stonewall Jackson's Headquarters

Winchester Historic District Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Aug 31 to Sep 1
CA $163
CA $185 total
Aug 31 - Sep 1
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)
"Bed comfy, dinner delicious. Lovely ambiance in lobby and enjoyed pool."

Reviewed on Aug. 10, 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is CA $142 per night from Sep 1 to Sep 2
CA $142
CA $154 total
Sep 1 - Sep 2
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! (2,127 reviews)
"Loved this hotel Clean, friendlt staff, great breakfast and dog friendly"

Reviewed on Aug. 14, 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
The price is CA $119 per night from Aug 24 to Aug 25
CA $119
CA $133 total
Aug 24 - Aug 25
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! (1,002 reviews)
"Bed comfort"

Reviewed on Aug. 12, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
The price is CA $103 per night from Sep 1 to Sep 2
CA $103
CA $112 total
Sep 1 - Sep 2
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! (1,317 reviews)
"Very quiet, carpets felt somewhat yuckie bc it is a pet place. Air conditioning worked very well."

Reviewed on Aug. 12, 2025

Microtel Inn & Suites by Wyndham Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive, Winchester, VA
The price is CA $140 per night from Aug 22 to Aug 23
CA $140
CA $152 total
Aug 22 - Aug 23
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.8/10 Excellent! (860 reviews)
"Hotel was near highway, gas station and other convenient items. Room was comfortable and clean. Staff was friendly and helpful"

Reviewed on Aug. 15, 2025

Courtyard by Marriott Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
The price is CA $93 per night from Sep 1 to Sep 2
CA $93
CA $103 total
Sep 1 - Sep 2
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! (1,003 reviews)
"Great location, clean, comfortable."

Reviewed on Aug. 13, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
See all 370 properties in Winchester Historic District
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 Winchester Historic District

Default Image

Old Town Winchester

Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

Old Town Winchester

Winchester Historic District

Choose two or more items and save on your trip: