Winchester Historic District Travel Guide

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 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
Jim Barnett park

Jim Barnett Park

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the cosy cafes 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 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

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

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

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 ฿3,967 per night from 30 Mar to 31 Mar
฿3,967
฿4,495 total
30 Mar - 31 Mar
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,001 reviews)
Location of hotel is great for walking to restaurants and shops.

Reviewed on 18 Mar 2026

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 ฿3,059 per night from 29 Mar to 30 Mar
฿3,059
฿3,427 total
29 Mar - 30 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,003 reviews)
Yes

Reviewed on 18 Mar 2026

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 ฿3,477 per night from 24 Mar to 25 Mar
฿3,477
฿3,784 total
24 Mar - 25 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,272 reviews)
Nice room, friendly staff

Reviewed on 17 Mar 2026

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 ฿2,628 per night from 12 Apr to 13 Apr
฿2,628
฿2,859 total
12 Apr - 13 Apr
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,000 reviews)
Yes the kitchen was a blessing

Reviewed on 16 Mar 2026

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 ฿2,805 per night from 24 Mar to 25 Mar
฿2,805
฿3,052 total
24 Mar - 25 Mar
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 ...
9.2/10 Wonderful! (1,445 reviews)
Quick over night while traveling. Everything we needed

Reviewed on 19 Mar 2026

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 ฿3,344 per night from 29 Mar to 30 Mar
฿3,344
฿3,789 total
29 Mar - 30 Mar
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! (1,000 reviews)
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel

Reviewed on 15 Mar 2026

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 neighbourhoods around Winchester Historic District

The Courthouse in Winchester, Virginia.

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