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 ฿4,318 per night from 11 Oct to 12 Oct
฿4,318
฿4,893 total
11 Oct - 12 Oct
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 ฿2,285 per night from 24 Sept to 25 Sept
฿2,285
฿2,521 total
24 Sept - 25 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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,232 per night from 11 Oct to 12 Oct
฿3,232
฿3,597 total
11 Oct - 12 Oct
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! (1,005 reviews)
"Hotel was very clean and breakfast was delicious with a lot of options"
Reviewed on 22 Sept 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,789 per night from 27 Sept to 28 Sept
฿3,789
฿4,217 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 ...
9.2/10 Wonderful! (2,278 reviews)
"Friendly, clean, what more can you ask?!"
Reviewed on 21 Sept 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is ฿3,069 per night from 7 Oct to 8 Oct
฿3,069
฿3,415 total
7 Oct - 8 Oct
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! (1,000 reviews)
"Location was very convenient and included inside access to 24hr Denny’s. Parking lot adjacent to an Exxon. Hot breakfast, hard boiled eggs, English"
Reviewed on 22 Sept 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿3,294 per night from 24 Sept to 25 Sept
฿3,294
฿3,666 total
24 Sept - 25 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! (1,450 reviews)
"The room was fine, not lavish but comfortable. Breakfast was adequate, tasted good but a little cool."
Reviewed on 22 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.
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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 Shenandoah Valley Discovery Museum.
