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

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

Handley Regional Library
Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

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.

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 savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

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.

Bright Box Theater

Winchester Little Theater

Enjoy a show at Winchester Little Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Winchester Little Theater

Stonewall Jackson's Headquarters

Find out about the history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Visit the cosy cafes or top-notch restaurants in this walkable area.

Stonewall Jackson's Headquarters

Top hotels in Winchester Historic District

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
The price is S$184 per night from 2 Oct to 3 Oct
S$184
per night
2 Oct - 3 Oct
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! (1,005 reviews)
"Always enjoy our stay at the GW Hotel. We were upgraded to a Junior Suite with a jacuzzi tub — an added bonus! It is conveniently located just a short walk to the pedestrian only downtown shops and restaurants. We will surely return when we are in the area."

Reviewed on 17 Sept, 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 S$151 per night from 28 Sept to 29 Sept
S$151
per night
28 Sept - 29 Sept
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! (2,152 reviews)
"Easy access to the highway as we passed through."

Reviewed on 13 Sept, 2025

La Quinta Inn & Suites by Wyndham Winchester
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 S$120 per night from 29 Sept to 30 Sept
S$120
per night
29 Sept - 30 Sept
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! (1,345 reviews)
"Very nice place to stay. Everything is perfectly placed and the amenities were good."

Reviewed on 21 Sept, 2025

Microtel 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 S$134 per night from 28 Sept to 29 Sept
S$134
per night
28 Sept - 29 Sept
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! (1,008 reviews)
Excellent hotel.
"The hotel was very nice and the staff was great! Check-in was easy and very helpful. We had our breakfast included which worked out well. Tina, our server, was above and beyond. She was so friendly and offered my husband a few suggestions which was wonderful. Highly recommend anyone staying ..."

Reviewed on 16 Sept, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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
Fully refundableReserve now, pay when you stay
The price is S$102 per night from 30 Sept to 1 Oct
S$102
per night
30 Sept - 1 Oct
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! (1,011 reviews)
"we were above the main entrance and I am a light sleeper, I could hear the entrance doors and noise. The hotel is conveniently located, clean, a comfortable bed and complimentary breakfast !!"

Reviewed on 17 Sept, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET, Winchester, VA
The price is S$162 per night from 25 Sept to 26 Sept
S$162
per night
25 Sept - 26 Sept
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! (724 reviews)
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Reviewed on 16 Sept, 2025

SpringHill Suites by Marriott Winchester
See all 375 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

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Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

Old Town Winchester

Winchester Historic District