Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Things to do
Shenandoah Tour: Self-Guided Drive
฿557
per traveller
98% of travellers recommend
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is ฿4,290 per night from 16 Sept to 17 Sept
฿4,290
฿4,861 total
16 Sept - 17 Sept
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! (1,002 reviews)
"1000 percent stay here!"
Reviewed on 9 Sept 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,536 per night from 28 Sept to 29 Sept
฿2,536
฿2,874 total
28 Sept - 29 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! (1,002 reviews)
"This hotel is very satisfactory other than the soft water. Please add less water softener!"
Reviewed on 9 Sept 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿3,389 per night from 11 Oct to 12 Oct
฿3,389
฿3,871 total
11 Oct - 12 Oct
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! (1,001 reviews)
"We stayed at the hotel for at least a week. Must say the coffee served in the restaurant during breakfast was outstanding. However, being eggetarians, the breakfast had the same protein option (scrambled egg) everyday - this meant we consumed the same items throughout the week, which was less than ..."
Reviewed on 9 Sept 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,076 per night from 27 Sept to 28 Sept
฿3,076
฿3,424 total
27 Sept - 28 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 helpful staff in their reviews. ...
9.2/10 Wonderful! (1,000 reviews)
"Very clean , comfortable. Decent breakfast. Friendly staff"
Reviewed on 8 Sept 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,751 per night from 13 Sept to 14 Sept
฿3,751
฿4,175 total
13 Sept - 14 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 ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,843 per night from 13 Sept to 14 Sept
฿2,843
฿3,164 total
13 Sept - 14 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! (1,462 reviews)
"Great service, nice complementary breakfast and very clean hotel."
Reviewed on 10 Sept 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.
Check Old Town Winchester hotel availability
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 Shenandoah Valley Discovery Museum.
