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 Shenandoah Valley Discovery Museum.

Winchester Historic District
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is NZ$126 per night from 21 July to 22 July
NZ$126
21 July - 22 July
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,102 reviews)
"It was in a very convenient location."

Reviewed on 12 Jul. 2025

Travelodge 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 NZ$211 per night from 21 July to 22 July
NZ$211
21 July - 22 July
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,084 reviews)
"Always good! On Hotel.com we can read free breakfast every day 6am to 9am. So, on weekend the breakfast begin at 7am. That was too late for us."

Reviewed on 13 Jul. 2025

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 NZ$167 per night from 27 July to 28 July
NZ$167
27 July - 28 July
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"Staff was courteous and helpful."

Reviewed on 9 Jul. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 1,999 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 WiFi, free parking, and daily housekeeping. Popular attractions Paw Paw Tunnel and Chesapeake and Ohio Canal ...
10/10 Exceptional! (3 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
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
10/10 Exceptional! (42 reviews)
"Excellent stay! Great space, privacy, clean."

Reviewed on 13 Jul. 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Rileyville
Stay at this cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley Public Library are located ...
9.8/10 Exceptional! (284 reviews)
Anniversary at The Chalet
"The Chalet offers a variety of cozy spots to enjoy an anniversary weekend -- outside on the deck with a great view of the mountains, a hot tub for soothing legs tired from hiking, a screened-in porch, and a mini living room w TV and streaming. We enjoyed relaxing in all of these spots, plus cooking ..."

Reviewed on 7 Jul. 2025

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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

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

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

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

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

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

Activities

Shenandoah National Park Self-Driving Audio Tour

Shenandoah Tour: Self-Guided Drive

NZ$28
per traveller
96% of travellers recommend
Shenandoah Tour: Self-Guided Drive
See all activities in Winchester

Cities near Winchester

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Stephens City

Photo by Paul Meola

Gore

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