Winchester Historic District Travel Guide

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 Rp2.119.868 per night from 5 Oct to 6 Oct
Rp2.119.868
Rp2.401.810 total
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (1,010 reviews)
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..."

Reviewed on 24 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 Rp1.812.893 per night from 5 Oct to 6 Oct
Rp1.812.893
Rp1.972.429 total
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,166 reviews)
"Friendly front desk..needed additional pillow and blanket ..got immediate response"

Reviewed on 23 Sept 2025

La Quinta Inn & Suites by Wyndham Winchester
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
The price is Rp1.472.526 per night from 5 Oct to 6 Oct
Rp1.472.526
Rp1.668.372 total
5 Oct - 6 Oct
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,011 reviews)
A good night"s stay.
"Clean, spacious, comfy, nice staff."

Reviewed on 20 Sept 2025

Hampton Inn Winchester-University/Mall Area
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 Rp1.405.992 per night from 26 Oct to 27 Oct
Rp1.405.992
Rp1.529.720 total
26 Oct - 27 Oct
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,346 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
Fully refundable
The price is Rp1.556.634 per night from 12 Oct to 13 Oct
Rp1.556.634
Rp1.743.932 total
12 Oct - 13 Oct
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,013 reviews)
"It was OK, but for some reason they use a very sweet pungent carpet deodorizer that was too strong for us."

Reviewed on 24 Sept 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is Rp1.205.136 per night from 1 Oct to 2 Oct
Rp1.205.136
Rp1.311.255 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,097 reviews)
"Clean room"

Reviewed on 20 Sept 2025

Travelodge by Wyndham Winchester
See all 378 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