Winchester Historic District Travel Guide

Tourist Guide

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 cosy cafes or top-notch restaurants 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 cosy cafes or top-notch restaurants 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 top-notch restaurants or cosy cafes in this walkable area.

Stonewall Jackson's Headquarters

Activities

Shenandoah National Park Self-Driving Audio Tour

Shenandoah Tour: Self-Guided Drive

AU$22
per traveller
96% of travellers recommend
Shenandoah Tour: Self-Guided Drive
See all activities in Winchester

Our pick of the best 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
The price is AU$219 per night from 21 July to 22 July
AU$219
21 July - 22 July
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! (1,005 reviews)
"Hotel was very nice. Service was good and it was clean and convenient."

Reviewed on 14 Jul. 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 AU$192 per night from 22 July to 23 July
AU$192
22 July - 23 July
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 ...
9/10 Wonderful! (2,084 reviews)
"Always good! On Hotel.com we can read free breakfast every day 6am to 9am. So, on weekend the breakfast begin at 7am. That was too late for us."

Reviewed on 13 Jul. 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is AU$114 per night from 20 July to 21 July
AU$114
20 July - 21 July
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! (1,102 reviews)
"It was in a very convenient location."

Reviewed on 12 Jul. 2025

Travelodge 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 AU$153 per night from 27 July to 28 July
AU$153
27 July - 28 July
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)
"Staff was courteous and helpful."

Reviewed on 9 Jul. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is AU$161 per night from 27 July to 28 July
AU$161
27 July - 28 July
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 breakfast and the helpful ...
9.4/10 Exceptional! (1,008 reviews)
"Excellent place to stay. This is our 2nd time and was great both times. I recommend."

Reviewed on 14 Jul. 2025

Comfort Inn & Suites
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 AU$149 per night from 20 July to 21 July
AU$149
20 July - 21 July
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! (1,298 reviews)
"The room was nice and the bed was comfortable"

Reviewed on 12 Jul. 2025

Microtel Inn & Suites by Wyndham Winchester
See all 365 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 Travel Guide

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