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 ฿4,309 per night from 20 Sept to 21 Sept
฿4,309
฿4,882 total
20 Sept - 21 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! (1,012 reviews)
"The shower was the best I had ever experienced. the pressure and water volume was awesome."
Reviewed on 13 Sept 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,547 per night from 11 Oct to 12 Oct
฿2,547
฿2,886 total
11 Oct - 12 Oct
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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,090 per night from 27 Sept to 28 Sept
฿3,090
฿3,439 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! (1,004 reviews)
"This hotel was very clean. There wasn't anything we needed that we didn't have. The bed wasn't the most comfortable that we have experienced on an 11 day trip, but it was adequate, and we slept fine. Would definitely stay at a TRU hotel again!"
Reviewed on 12 Sept 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is ฿2,280 per night from 14 Sept to 15 Sept
฿2,280
฿2,515 total
14 Sept - 15 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! (1,072 reviews)
"Staff at check in was OK. Neither friendly or unfriendly . Location was a little sketchy but the room and bedding were clean 👌."
Reviewed on 13 Sept 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,831 per night from 27 Sept to 28 Sept
฿3,831
฿4,264 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 breakfast and the helpful staff ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is ฿2,781 per night from 20 Sept to 21 Sept
฿2,781
฿3,095 total
20 Sept - 21 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! (1,005 reviews)
"Staff were kind and the room was nice and clean. Beds were comfortable. Room was spacious. We loved our stay and we stay again the next time we visit!"
Reviewed on 13 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.
