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! (1,003 reviews)
"I really enjoyed the property. Extremely convenient to downtown attractions while being relatively quiet and nice. Staff was very helpful, room was lovely and clean and the pool was gorgeous."
Reviewed on Oct 24, 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
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 8 to Nov 9
$93 total
Nov 8 - Nov 9
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 ...
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 ...
8.2/10 Very Good! (1,018 reviews)
"Ok stay, free breakfast was good ( just there for a transit)."
Reviewed on Oct 24, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$107 nightly
The price is $119 total per night from Oct 26 to Oct 27
$119 total
Oct 26 - Oct 27
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.
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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