Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is ฿4,037 per night from 27 Aug to 28 Aug
฿4,037
฿4,574 total
27 Aug - 28 Aug
includes taxes & fees
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 clean rooms ...
9.4/10 Exceptional! (1,006 reviews)
"This is a great stop and a beautiful place. Highly recommended and will stay there again when in the area."
Reviewed on 17 Aug 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,605 per night from 14 Sept to 15 Sept
฿2,605
฿2,952 total
14 Sept - 15 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,010 reviews)
"The staff was so friendly and the hotel was very clean"
Reviewed on 18 Aug 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿3,073 per night from 23 Aug to 24 Aug
฿3,073
฿3,519 total
23 Aug - 24 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,012 reviews)
"Clean and comfortable room. Great bed, pillows and an amazing shower."
Reviewed on 18 Aug 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,390 per night from 23 Aug to 24 Aug
฿3,390
฿3,773 total
23 Aug - 24 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,890 per night from 30 Aug to 31 Aug
฿2,890
฿3,217 total
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,437 reviews)
"Everything was very clean and new. The staff were all very helpful and nice. The road noise from the highway was disturbing. The water pressure was terrible and the 24 hour coffee was rarely fresh. I would also have liked more than one pillow."
Reviewed on 17 Aug 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,224 per night from 26 Aug to 27 Aug
฿3,224
฿3,589 total
26 Aug - 27 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,008 reviews)
"Very nice newer hotel. Only complaints were there were no shelves in the shower to sit your soap and shampoo. There was body wash shampoo and conditioner stuck on the wall but I like to bring my own. Also being from the south, I was very excited that they had grits for breakfast but apparently making ..."
Reviewed on 18 Aug 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 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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.
