Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is SAR 490 per night from Oct 5 to Oct 6
SAR 490
SAR 555 total
5 Oct - 6 Oct
includes taxes & fees
Book a 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 ...
9.4/10 Exceptional! (1,011 reviews)
"Clean room, great shower. A block from the walking mall with lots of food, shopping, and a few breweries. Highly recommend."
Reviewed on 28 September 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is SAR 259 per night from Sep 30 to Oct 1
SAR 259
SAR 286 total
30 Sep - 1 Oct
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! (1,081 reviews)
"Clean room"
Reviewed on 29 September 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is SAR 336 per night from Oct 5 to Oct 6
SAR 336
SAR 374 total
5 Oct - 6 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,004 reviews)
"Very nice motel. I plan to stay there again, the next time I drive on the Summit Point race track nearby."
Reviewed on 28 September 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is SAR 424 per night from Oct 1 to Oct 2
SAR 424
SAR 472 total
1 Oct - 2 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,273 reviews)
"The parking lot has no control. Everyone parked how ever they want to park. The some of the trailers parked and blocked 6 parking space"
Reviewed on 28 September 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is SAR 316 per night from Oct 25 to Oct 26
SAR 316
SAR 352 total
25 Oct - 26 Oct
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is SAR 381 per night from Oct 25 to Oct 26
SAR 381
SAR 425 total
25 Oct - 26 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (1,460 reviews)
"Top notch hotel! We had a great stay. Shelby was awesome and very helpful!"
Reviewed on 29 September 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 and neighborhoods for the activities you enjoy most.
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.
