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 ฿4,007 per night from 7 Sept to 8 Sept
฿4,007
฿4,540 total
7 Sept - 8 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 ...
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿3,254 per night from 27 Sept to 28 Sept
฿3,254
฿3,721 total
27 Sept - 28 Sept
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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is ฿2,263 per night from 31 Aug to 1 Sept
฿2,263
฿2,496 total
31 Aug - 1 Sept
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,084 reviews)
"The room was spacious and clean. It appeared to have been updated recently. No carpet was a plus. The bathroom was clean but had a bit of an odor ( I think from the shower curtain). The bed was super comfy and had newer linens. Parking was ample and easy. Staff were friendly. Breakfast was basic ..."
Reviewed on 27 Aug 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,225 per night from 30 Aug to 31 Aug
฿3,225
฿3,589 total
30 Aug - 31 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 ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,536 per night from 28 Sept to 29 Sept
฿2,536
฿2,873 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)
"Great stay! Very clean and the staff was great."
Reviewed on 26 Aug 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,867 per night from 30 Aug to 31 Aug
฿2,867
฿3,190 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! (1,447 reviews)
"The property was clean! The rooms were comfortable and clean. Didn't like the small hard bed pillows! And when there's two people in the room, I wish they would provide two packets of regular coffee. Not one regular coffee and one decaf."
Reviewed on 25 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.
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 Winchester Little Theater.
