Old Town Winchester Travel Guide

Winchester

The Courthouse in Winchester, Virginia.
Old Town Winchester
Old Town Winchester
Old Town Winchester
Old Town Winchester

Popular places to visit

Museum of the Shenandoah Valley

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

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

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

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 savour the top-notch restaurants.

Old Court House Civil War Museum

Top hotels in Old Town Winchester

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 Rp2.266.917 per night from 26 May to 27 May
Rp2.266.917
Rp2.568.417 total
26 May - 27 May
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! (1,007 reviews)
Toilets are low

Reviewed on 7 May 2026

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is Rp1.448.692 per night from 31 May to 1 Jun
Rp1.448.692
Rp1.641.435 total
31 May - 1 Jun
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,027 reviews)
It was a nice hotel and very worth the price we paid! The Continental breakfast was great and had a lot of choices. The staff was very attentive as well.

Reviewed on 7 May 2026

Spark by Hilton Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
The price is Rp1.230.643 per night from 10 May to 11 May
Rp1.230.643
Rp1.338.974 total
10 May - 11 May
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. ...
8.6/10 Excellent! (1,058 reviews)
Clean and comfortable. Good for the price.

Reviewed on 6 May 2026

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 Rp1.663.968 per night from 24 May to 25 May
Rp1.663.968
Rp1.862.431 total
24 May - 25 May
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! (1,010 reviews)
Perfect hotel. I love this hotel.

Reviewed on 5 May 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 Rp1.664.835 per night from 10 May to 11 May
Rp1.664.835
Rp1.811.299 total
10 May - 11 May
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! (1,452 reviews)
Quiet. Very nice front desk lady gave us extra blankets when we asked. Great breakfast!

Reviewed on 6 May 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 Rp2.114.626 per night from 10 May to 11 May
Rp2.114.626
Rp2.300.782 total
10 May - 11 May
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! (2,278 reviews)
The facility was clean and safe . We were very comfortable there . When I came down in the morning around 5:30 there was no coffee . Not a big deal but it would of been nice .

Reviewed on 8 May 2026

La Quinta Inn & Suites by Wyndham Winchester
See all 370 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 neighbourhoods 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 Travel Guide