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

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
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

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

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
Fully refundableReserve now, pay when you stay
The price is Rp2.050.913 per night from 25 Feb to 26 Feb
Rp2.050.913
Rp2.323.684 total
25 Feb - 26 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 Rp1.676.921 per night from 17 Feb to 18 Feb
Rp1.676.921
Rp1.824.489 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 Rp1.175.020 per night from 17 Feb to 18 Feb
Rp1.175.020
Rp1.278.422 total
17 Feb - 18 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
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 19 Feb to 20 Feb
Rp1.416.076
Rp1.540.690 total
19 Feb - 20 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
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 16 Feb to 17 Feb
Rp1.453.939
Rp1.581.886 total
16 Feb - 17 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
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 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