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 ฿4,039 per night from 23 Aug to 24 Aug
฿4,039
฿4,577 total
23 Aug - 24 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! (1,018 reviews)
"Great walking location to everything. Fancy historic building."
Reviewed on 9 Aug 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿3,075 per night from 13 Aug to 14 Aug
฿3,075
฿3,521 total
13 Aug - 14 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! (1,021 reviews)
"Nice sized room & bathroom. Nice shower. Dove shampoo. Good tasting breakfast nice polite staff I worth the price.not much noise I slept well. The pool looked fine. There was a bar but I didnt use any t. I really enjoyed my time there"
Reviewed on 10 Aug 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,548 per night from 30 Aug to 31 Aug
฿2,548
฿2,887 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! (1,018 reviews)
"The staff was amazing. Best check in ever. Breakfast is very basic but it's OK since there are some great places for breakfast in town worth going."
Reviewed on 10 Aug 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,571 per night from 6 Sept to 7 Sept
฿3,571
฿3,974 total
6 Sept - 7 Sept
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 ...
9.2/10 Wonderful! (2,276 reviews)
"I usually have a pretty decent stay, but after driving almost 6 hours and had my three dogs and luggage - the bed was unmade and they were dirty. They put me in another room but dragging all my stuff at 9 pm was not fun. I don’t know if I’ll go back."
Reviewed on 9 Aug 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,670 per night from 23 Aug to 24 Aug
฿2,670
฿2,971 total
23 Aug - 24 Aug
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very good! (1,006 reviews)
"Clean room and breakfast buffet area"
Reviewed on 10 Aug 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿3,068 per night from 16 Aug to 17 Aug
฿3,068
฿3,415 total
16 Aug - 17 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! (1,448 reviews)
"Nice clean room and facilities. They made traveling with our dog easy!"
Reviewed on 10 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 Bright Box Theater and Stonewall Jackson's Headquarters.
