Old Town Winchester, VA

Winchester

The Courthouse in Winchester, Virginia.
The Courthouse in Winchester, 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

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Jim Barnett park

Jim Barnett Park

4/5(1 review)

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

Jim Barnett Park

Shenandoah Valley Discovery Museum

4.5/5(11 reviews)

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

4.5/5(4 reviews)

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

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Handley Regional Library

Old Court House Civil War Museum

You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Old Court House Civil War Museum

Old Town Winchester 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 ₩185,559 per night from Feb 1 to Feb 2
₩185,559
₩210,239 total
Feb 1 - Feb 2
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 ...
9.2/10 Wonderful! (1,003 reviews)
Everything was wonderful and our room was perfect

Reviewed on Jan 17, 2026

The George Washington Hotel, A Wyndham Grand Hotel
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 ₩119,555 per night from Jan 26 to Jan 27
₩119,555
₩130,076 total
Jan 26 - Jan 27
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! (1,438 reviews)
Perfect for a single night, relatively clean, very friendly staff and decent breakfast.

Reviewed on Jan 18, 2026

Microtel Inn & Suites by Wyndham Winchester
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 ₩134,499 per night from Jan 26 to Jan 27
₩134,499
₩146,334 total
Jan 26 - Jan 27
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! (2,248 reviews)
Clean room. Friendly and helpful staff.

Reviewed on Jan 21, 2026

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

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
The price is ₩143,407 per night from Feb 8 to Feb 9
₩143,407
₩156,027 total
Feb 8 - Feb 9
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! (1,098 reviews)
All of the above

Reviewed on Jan 21, 2026

Comfort Inn & Suites Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
The price is ₩120,683 per night from Feb 20 to Feb 21
₩120,683
₩131,303 total
Feb 20 - Feb 21
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,000 reviews)
The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ...

Reviewed on Jan 18, 2026

Quality Inn 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 ₩148,974 per night from Feb 8 to Feb 9
₩148,974
₩168,788 total
Feb 8 - Feb 9
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)
Pet friendly and they provided a goodie bag for my dog - very welcoming.

Reviewed on Jan 13, 2026

Hampton Inn Winchester-University/Mall Area
See all 369 properties in Old Town Winchester
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 Old Town Winchester

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

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District

Old Town Winchester, VA