Winchester

Travel Guide

Winchester
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 known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

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 CA $141 per night from Sep 1 to Sep 2
CA $141
CA $154 total
Sep 1 - Sep 2
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 ...
9.2/10 Wonderful! (2,137 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."

Reviewed on Aug. 25, 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
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from Sep 15 to Sep 16
CA $109
CA $119 total
Sep 15 - Sep 16
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,326 reviews)
"It was a great experiencia. It was really clean and the staff was exactly friendly and accommodated"

Reviewed on Aug. 24, 2025

Microtel 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 CA $113 per night from Sep 1 to Sep 2
CA $113
CA $127 total
Sep 1 - Sep 2
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! (1,008 reviews)
"Clean and staff was great."

Reviewed on Aug. 23, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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.
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Edinburg
Stay at this vacation home in Woodstock. Enjoy a garden, laundry facilities, and patios. Popular attractions Shenandoah Vineyards and Edinburg Mill Museum are ...
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
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 ...
9.6/10 Exceptional! (8 reviews)
"Very nice"

Reviewed on Aug. 9, 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 ...
Dreamtime - Modern A-frame Cabin w/ Hot tub
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

Cities near Winchester