Winchester Historic District Travel Guide

Winchester

Buildings and streets in the historic part of the ancient city of Winchester in Virginia.
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.

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 cosy cafes or top-notch restaurants 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

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

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

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

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

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 Rp2.056.045 per night from 22 Feb to 23 Feb
Rp2.056.045
Rp2.329.499 total
22 Feb - 23 Feb
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 ...
9.2/10 Wonderful! (1,001 reviews)
Clean nice room Great location for restaurants

Reviewed on 28 Jan 2026

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 Rp1.681.117 per night from 17 Feb to 18 Feb
Rp1.681.117
Rp1.829.055 total
17 Feb - 18 Feb
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! (2,263 reviews)
The room was very large and spotless. Clean and filled with plenty towels!

Reviewed on 10 Feb 2026

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 Rp1.177.960 per night from 15 Feb to 16 Feb
Rp1.177.960
Rp1.281.620 total
15 Feb - 16 Feb
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 helpful staff and the clean rooms in their reviews. ...
8.4/10 Very Good! (1,081 reviews)
Room was good for the price, staff was friendly and helpful

Reviewed on 4 Feb 2026

Travelodge 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 Rp1.453.939 per night from 22 Feb to 23 Feb
Rp1.453.939
Rp1.581.886 total
22 Feb - 23 Feb
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! (1,446 reviews)
The only thing that disappointed me is that the breakfast potatoes and omelets were quite spice. I was unable to eat them. However, the room was excellent.

Reviewed on 10 Feb 2026

Microtel Inn & Suites by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
The price is Rp1.416.076 per night from 20 Feb to 21 Feb
Rp1.416.076
Rp1.540.690 total
20 Feb - 21 Feb
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,000 reviews)
Very clean

Reviewed on 10 Feb 2026

Quality Inn Winchester
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

3 out of 5
5 Caroline Drive Front Royal VA
The price is Rp1.918.392 per night from 22 Feb to 23 Feb
Rp1.918.392
Rp2.149.642 total
22 Feb - 23 Feb
includes taxes & fees
Stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (562 reviews)
Over all great! just wish the break was a little better.

Reviewed on 8 Feb 2026

TownePlace Suites by Marriott Front Royal
See all 383 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