Winchester Travel Guide

Tourist 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 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 £55 per night from 9 Jul to 10 Jul
£55
9 Jul - 10 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! (1,116 reviews)
"Good place for the price, complimentary breakfast was nice"

Reviewed on 3 Jul 2025

Travelodge 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 £73 per night from 20 Jul to 21 Jul
£73
20 Jul - 21 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"The room was nice and the beds comfortable; however, people were out in the hallway late at night making a lot of noise. Also, we prefer a buffet breakfast - the served breakfast just takes too long for people on the road for work."

Reviewed on 5 Jul 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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 £88 per night from 6 Jul to 7 Jul
£88
6 Jul - 7 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! (2,067 reviews)
"I’ve had very pleasant experiences at this property. Great staff and great location right off of the highway with restaurants and shopping nearby."

Reviewed on 3 Jul 2025

La Quinta Inn & Suites by Wyndham 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 ...
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, 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! (41 reviews)
Lovely Forest Retreat with All the Creature Comforts
"My husband and I visited for our anniversary. The cabin is lovely - beautifully renovated, thoughtfully outfitted, and situated in a lovely forested setting. The king-sized bed was the most comfortable bed that I have slept on away from home. The hot tub uses a saltwater system which is so much more ..."

Reviewed on 24 May 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville, VA
Stay at this cabin in Rileyville. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in their reviews. Popular attractions ...
9.8/10 Exceptional! (309 reviews)
Walden Wonderful
"Walden was exactly as advertised. We loved the cozy atmosphere and creature comforts. Due to rainy weather we did not get to utilize a lot of the outdoor and riverside amenities but recognized them for being available had the weather cooperated. Derek was very responsive to any needs we had. We loved ..."

Reviewed on 23 May 2025

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River 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