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 cosy cafes or top-notch restaurants in this walkable area.

Handley Regional Library
Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(1 review)

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

Shenandoah Valley Discovery Museum

4/5(1 review)

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 top-notch restaurants or cosy cafes 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 Rp2.063.762 per night from 27 Jul to 28 Jul
Rp2.063.762
Rp2.338.333 total
27 Jul - 28 Jul
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! (1,003 reviews)
"Hotel was very nice. Service was good and it was clean and convenient."

Reviewed on 14 Jul 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
Fully refundableReserve now, pay when you stay
The price is Rp1.689.791 per night from 30 Jul to 31 Jul
Rp1.689.791
Rp1.838.492 total
30 Jul - 31 Jul
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! (2,086 reviews)
"Clean room, comfortable bed and friendly staff."

Reviewed on 23 Jul 2025

La Quinta Inn & Suites 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 Rp1.342.708 per night from 17 Aug to 18 Aug
Rp1.342.708
Rp1.460.866 total
17 Aug - 18 Aug
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! (1,315 reviews)
DA BOMB
"IT WAS A VERY NICE HOTEL. GREAT LOCATION & LIKE BRAND NEW (OPEN 3YRS BUT NO WEAR & TEAR).)"

Reviewed on 21 Jul 2025

Microtel 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 Rp1.124.355 per night from 27 Jul to 28 Jul
Rp1.124.355
Rp1.223.429 total
27 Jul - 28 Jul
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! (1,094 reviews)
"This was a perfect one night stop on my road trip. The room was large and clean. However, I think the cleaner they use for the floor leaves a residue. I dared to walk on it barefoot and it was a tad slippery, so I recommend wearing slippers. It was quiet and pet friendly! There is a $15 pet fee."

Reviewed on 21 Jul 2025

Travelodge 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
The price is Rp1.450.255 per night from 3 Aug to 4 Aug
Rp1.450.255
Rp1.626.893 total
3 Aug - 4 Aug
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! (1,020 reviews)
"Overall very good experience."

Reviewed on 23 Jul 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is Rp1.578.986 per night from 3 Aug to 4 Aug
Rp1.578.986
Rp1.717.938 total
3 Aug - 4 Aug
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 ...
9.4/10 Exceptional! (1,014 reviews)
"Love the location and stay here often. My only problem is the mattress is horrible. May be time for an upgrade."

Reviewed on 24 Jul 2025

Comfort Inn & Suites
See all 365 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