Winchester Historic District, VA

Winchester

Buildings and streets in the historic part of the ancient city of Winchester in Virginia.
Handley Library
A nice 3 block outdoor downtown shopping area with dining and bars also.
Holiday shopping in Winchester.
Took a day trip to Old Town Winchester for some shopping on Shop Small Saturday.

Popular places to visit

Gardens at Glen Burnie House.

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.

Museum of the Shenandoah Valley
Jim Barnett park

Jim Barnett Park

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Jim Barnett Park

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

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 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

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 NT$4,290 per night from Mar 29 to Mar 30
NT$4,290
NT$4,861 total
Mar 29 - Mar 30
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,000 reviews)
Location of hotel is great for walking to restaurants and shops.

Reviewed on 2026/3/18

The George Washington Hotel, A Wyndham Grand Hotel
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 NT$2,815 per night from Apr 5 to Apr 6
NT$2,815
NT$3,159 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this 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)
Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service.

Reviewed on 2026/3/23

Holiday Inn Winchester Se-Historic Gateway by IHG
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 NT$3,426 per night from Mar 29 to Mar 30
NT$3,426
NT$3,728 total
Mar 29 - Mar 30
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 ...
9.2/10 Wonderful! (2,271 reviews)
Very nice would stay there again

Reviewed on 2026/3/26

La Quinta Inn & Suites by Wyndham Winchester
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
The price is NT$2,706 per night from Apr 9 to Apr 10
NT$2,706
NT$2,945 total
Apr 9 - Apr 10
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 ...
7.8/10 Good! (1,002 reviews)
The room was very clean. The staff are friendly. Nice place to stay.

Reviewed on 2026/3/23

Sleep Inn & Suites Winchester near University
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 NT$3,081 per night from Mar 30 to Mar 31
NT$3,081
NT$3,352 total
Mar 30 - Mar 31
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 ...
Microtel 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 NT$3,528 per night from Apr 20 to Apr 21
NT$3,528
NT$3,998 total
Apr 20 - Apr 21
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! (1,000 reviews)
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel

Reviewed on 2026/3/15

Hampton Inn Winchester-University/Mall Area
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 neighborhoods around Winchester Historic District

The Courthouse in Winchester, Virginia.

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, VA