Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$122 nightly
The price is $138 total per night from Aug 9 to Aug 10
$138 total
Aug 9 - Aug 10
Total with taxes and 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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $77 total per night from Aug 2 to Aug 3
$77 total
Aug 2 - Aug 3
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,057 reviews)
"W"
Reviewed on Jul 31, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
$90 nightly
The price is $100 total per night from Aug 30 to Aug 31
$100 total
Aug 30 - Aug 31
Total with taxes and 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 ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
$65 nightly
The price is $73 total per night from Aug 23 to Aug 24
$73 total
Aug 23 - Aug 24
Total with taxes and 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 ...
9/10 Wonderful! (1,004 reviews)
"no coffee maker"
Reviewed on Jul 31, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
$106 nightly
The price is $118 total per night from Aug 17 to Aug 18
$118 total
Aug 17 - Aug 18
Total with taxes and 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. ...
9.2/10 Wonderful! (1,003 reviews)
"Clean, friendly, easy check in!"
Reviewed on Jul 31, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$107 nightly
The price is $119 total per night from Aug 11 to Aug 12
$119 total
Aug 11 - Aug 12
Total with taxes and 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! (2,260 reviews)
"Very nice clean hotel"
Reviewed on Jul 31, 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.
Where to stay in Old Town Winchester
Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester
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.
Old Town Winchester, VA
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- Visit Bluemont
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- Bright Box Theater
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