Old Town Winchester, VA
Winchester
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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 5 to Nov 6
$148 total
Nov 5 - Nov 6
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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $78 total per night from Nov 1 to Nov 2
$78 total
Nov 1 - Nov 2
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
$84 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! (1,440 reviews)
"They had a very nice breakfast. The room was spacious and had a full kitchen."
Reviewed on Oct 26, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
$85 nightly
The price is $95 total per night from Nov 8 to Nov 9
$95 total
Nov 8 - Nov 9
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. ...
9.2/10 Wonderful! (1,004 reviews)
"Nice"
Reviewed on Oct 27, 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
$76 nightly
The price is $84 total per night from Nov 3 to Nov 4
$84 total
Nov 3 - Nov 4
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 ...
8.2/10 Very Good! (1,023 reviews)
"This was an amazing surprise 100% in every category. very clean rooms, every area smelled so fresh. Plenty of handicap accessible parking and guest rooms. Hot complimentary breakfast 7 AM - 10 AM; pancake machine, eggs, sausage, choice of bread, muffins, bagels, yogurt and cereals. Juice machine ..."
Reviewed on Oct 26, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$114 nightly
The price is $127 total per night from Nov 1 to Nov 2
$127 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 breakfast and the helpful ...
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.
Check Old Town Winchester hotel availability
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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