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 ฿4,356 per night from 27 Sept to 28 Sept
฿4,356
฿4,936 total
27 Sept - 28 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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is ฿2,306 per night from 20 Sept to 21 Sept
฿2,306
฿2,543 total
20 Sept - 21 Sept
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,074 reviews)
"Better breakfast"
Reviewed on 17 Sept 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,123 per night from 27 Sept to 28 Sept
฿3,123
฿3,476 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! (1,001 reviews)
"Staff were extremely friendly and the hotel looked brand new cleanliness wise!"
Reviewed on 17 Sept 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,460 per night from 20 Sept to 21 Sept
฿3,460
฿3,851 total
20 Sept - 21 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 ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is ฿2,812 per night from 24 Sept to 25 Sept
฿2,812
฿3,129 total
24 Sept - 25 Sept
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,004 reviews)
"Clean room, Denny's attached to hotel is very convenient. Continental breakfast included biscuits and gravy, specialty teas and juices. Though the hotel is fairly close to the road, the room was quiet. Will book again if we are in the area"
Reviewed on 17 Sept 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿3,021 per night from 20 Sept to 21 Sept
฿3,021
฿3,362 total
20 Sept - 21 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! (1,442 reviews)
"Very clean hotel and rooms. Breakfast was very good too!"
Reviewed on 18 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.
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.
