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
$130 nightly
The price is $148 total per night from Nov 1 to Nov 2
$148 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,001 reviews)
"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"
Reviewed on Oct 21, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $78 total per night from Oct 26 to Oct 27
$78 total
Oct 26 - Oct 27
Total with taxes and 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 ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
$83 nightly
The price is $93 total per night from Nov 22 to Nov 23
$93 total
Nov 22 - Nov 23
Total with taxes and 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! (1,435 reviews)
"The room was just ok; not any room in the bathroom to put anything so I had to store items on top of the toilet; breakfast was just mediocre."
Reviewed on Oct 23, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
$85 nightly
The price is $95 total per night from Nov 1 to Nov 2
$95 total
Nov 1 - Nov 2
Total with taxes and 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. ...
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
$76 nightly
The price is $84 total per night from Nov 1 to Nov 2
$84 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$103 nightly
The price is $114 total per night from Oct 25 to Oct 26
$114 total
Oct 25 - Oct 26
Total with taxes and 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! (2,270 reviews)
"Super clean, very quiet and excellent breakfast. Highly recommend."
Reviewed on Oct 23, 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 and neighborhoods 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.
Old Town Winchester, VA
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