Old Town Winchester
Winchester
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Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is CA $172 per night from Aug 13 to Aug 14
CA $172
CA $194 total
Aug 13 - Aug 14
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,000 reviews)
"The 20's decor and authentic details added to classy feel of the hotel. Unique Romanesque pool. 5 minute walk to the Pedestrian Mall."
Reviewed on Jul 28, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is CA $117 per night from Aug 23 to Aug 24
CA $117
CA $134 total
Aug 23 - Aug 24
includes taxes & fees
Book a stay at this 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)
"This site is fairly close to the Interstate and convenient for travelers. As expected, the Holiday Inn lived up to our expectations. The room was clean and comfortable. The staff was friendly. The breakfast was good and adequate. I would definitely stay here again should travel take me this way."
Reviewed on Jul 29, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is CA $144 per night from Aug 5 to Aug 6
CA $144
CA $160 total
Aug 5 - Aug 6
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 in our reviews. ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is CA $153 per night from Aug 2 to Aug 3
CA $153
CA $170 total
Aug 2 - Aug 3
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 breakfast and the helpful ...
9.2/10 Wonderful! (2,258 reviews)
"This property is being neglected. It could be a beautiful place but it appears to be uncared for. Carpets in hallways are dirty, elevator dirty and the walls are stained. This hotel is in desperate need of some TLC."
Reviewed on Jul 28, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is CA $137 per night from Aug 24 to Aug 25
CA $137
CA $153 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is CA $113 per night from Aug 17 to Aug 18
CA $113
CA $126 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very good! (1,002 reviews)
"The room was good. Most hotels you can hear the people in the next room but this one was quiet."
Reviewed on Jul 30, 2026
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.
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Where to stay in Old Town Winchester
Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most.
Photo by Fernando Begay
Open Photo by Fernando Begay
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Winchester Little Theater and Shenandoah Valley Discovery Museum.
