Old Town Winchester
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 CA $181 per night from Sep 27 to Sep 28
CA $181
CA $206 total
Sep 27 - Sep 28
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! (1,002 reviews)
"Everything was perfect! Highly recommended"
Reviewed on Sep 17, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is CA $96 per night from Sep 21 to Sep 22
CA $96
CA $106 total
Sep 21 - Sep 22
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! (1,073 reviews)
"We stay here a couple of times a year. Always super clean. Great place for the $. Breakfast is not as good as it used to be. Instant coffee. A lot of carbs c"
Reviewed on Sep 14, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is CA $130 per night from Sep 27 to Sep 28
CA $130
CA $145 total
Sep 27 - Sep 28
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. ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is CA $145 per night from Sep 20 to Sep 21
CA $145
CA $161 total
Sep 20 - Sep 21
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 ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
Fully refundable
The price is CA $117 per night from Sep 23 to Sep 24
CA $117
CA $130 total
Sep 23 - Sep 24
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 ...
9.4/10 Exceptional! (1,002 reviews)
"The hotel is conveniently located, clean, pleasant and very reasonably priced. It was just what we needed for an overnight stop with a dog."
Reviewed on Sep 16, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is CA $126 per night from Sep 22 to Sep 23
CA $126
CA $140 total
Sep 22 - Sep 23
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! (1,448 reviews)
"Room was clean. And well put together. Parking was plenty in a great spot. Staff were kind and friendly, very welcoming especially arriving after midnight."
Reviewed on Sep 16, 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.
