Old Town Winchester Travel Guide

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

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 top-notch restaurants or cosy cafes 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 Rp2.060.932 per night from 15 Mar to 16 Mar
Rp2.060.932
Rp2.335.037 total
15 Mar - 16 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! (1,006 reviews)
Room was clean but a lil noisy. We didn't have the best room location. Must have been close to a staff area

Reviewed on 2 Mar 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 Rp1.842.829 per night from 11 Mar to 12 Mar
Rp1.842.829
Rp2.004.999 total
11 Mar - 12 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! (2,284 reviews)
Room was great. Check in was easy.

Reviewed on 3 Mar 2026

La Quinta Inn & Suites 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 Rp1.484.384 per night from 15 Mar to 16 Mar
Rp1.484.384
Rp1.665.546 total
15 Mar - 16 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! (1,005 reviews)
Yes

Reviewed on 3 Mar 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 Rp1.715.476 per night from 15 Mar to 16 Mar
Rp1.715.476
Rp1.943.635 total
15 Mar - 16 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)
I sent a message to the Hotel as we had to head directly home - as my wife was feeling ill; but I'm not sure the Hotel received my message and canceled the reservation. I'm surprised I didn't get a response.

Reviewed on 18 Feb 2026

Hampton Inn Winchester-University/Mall Area
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3 out of 5
100 Hollywood Dr Charles Town WV
The price is Rp1.821.575 per night from 16 Mar to 17 Mar
Rp1.821.575
Rp2.208.865 total
16 Mar - 17 Mar
includes taxes & fees
Stay at this business-friendly hotel in Charles Town. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (544 reviews)
Had the breakfast which was very good with the selection that was offered very clean room

Reviewed on 2 Mar 2026

The Inn at Charles Town - Hollywood Casino
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 Rp1.430.406 per night from 15 Mar to 16 Mar
Rp1.430.406
Rp1.556.282 total
15 Mar - 16 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! (1,440 reviews)
I loved how clean the property was.

Reviewed on 4 Mar 2026

Microtel Inn & Suites by Wyndham Winchester
See all 374 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