Winchester Travel Guide

Tourist Guide

Winchester
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

Where to stay in Winchester

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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
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Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Winchester Historic District
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 £84 per night from 30 Jul to 31 Jul
£84
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 ...
9/10 Wonderful! (2,099 reviews)
"Nice spacious room and they had a good breakfast."

Reviewed on 27 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 £66 per night from 17 Aug to 18 Aug
£66
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! (1,321 reviews)
"Nice hotel. The dog fee is a bit high."

Reviewed on 27 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 £57 per night from 30 Jul to 31 Jul
£57
30 Jul - 31 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! (1,099 reviews)
"Good location great value friendly staff"

Reviewed on 27 Jul 2025

Travelodge by Wyndham Winchester
See all 2,001 properties in 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.
Canal Cabins

Canal Cabins

3 out of 5
143 Louie's Ln, Paw Paw, WV
Stay at this 3-star cabin in Paw Paw. Enjoy free Wi-Fi, free parking and daily housekeeping. Popular attractions Paw Paw Tunnel and Chesapeake and Ohio Canal ...
9.4/10 Exceptional! (6 reviews)
Great
"Great place, futon def too hard we shared the bed otherwise 10/10"

Reviewed on 30 Jun 2025

Canal Cabins
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs, WV
Stay at this cabin in Berkeley Springs. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
10/10 Exceptional! (44 reviews)
"Cutest little house in the woods. We enjoyed the hot tub under the stars, and the very comfortable bed. It was quiet and relaxing in this home, and it was so nice to have the essentials provided (like coffee, sugar, creamer, garbage bags, paper towels, detergent). Very close to the brewery, and to ..."

Reviewed on 16 Jul 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront

Star view cabin-Riverfront

Rileyville, VA
Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts and patios. Our guests praise the property condition in their reviews. Popular attractions ...
9.6/10 Exceptional! (291 reviews)
"Quiet and Peaceful just what we needed"

Reviewed on 21 Jul 2025

Star view cabin-Riverfront
See all properties in 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.

Popular places to visit

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
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

Winchester Medical Center

If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

Winchester Medical Center

Shenandoah University

Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah University

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Apple Blossom Mall

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

Cities near Winchester

Photo by Fernando Begay

Front Royal

Berkeley Springs State Park which includes a park

Berkeley Springs

Other places like Winchester