Find a Hotel in Old Town Winchester
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Top hotels in Old Town Winchester
SpringHill Suites by Marriott Winchester
280 MARKET STREET, Winchester, VA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $126 total per night from Oct 5 to Oct 6
$126 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
"Pleasant"
Reviewed on Sep 22, 2025
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $101 total per night from Sep 30 to Oct 1
$101 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
Great Accommodations
"No complaints, everything was perfect. Had an enjoyable overnight stay. We had a Saturday morning breakfast which was served between seven and 10. We arrived at nine. Rather slim pickings. Had one young lady trying to keep up with the inventory. She did her best."
Reviewed on Sep 21, 2025
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
$127 nightly
The price is $144 total per night from Oct 5 to Oct 6
$144 total
Oct 5 - Oct 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..."
Reviewed on Sep 24, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from Oct 5 to Oct 6
$118 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"The room was very well laid out. Beds were comfortable. Breakfast was standard fare but tasty. The serving staff were very efficient. We were pleasanty surprised with our first visit hetr. It is an ideal layover point when travelling onward to Shenandoah National Park"
Reviewed on Sep 22, 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $91 total per night from Oct 26 to Oct 27
$91 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests ...
"Very nice place to stay. Everything is perfectly placed and the amenities were good."
Reviewed on Sep 21, 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
$91 nightly
The price is $99 total per night from Oct 26 to Oct 27
$99 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
"It was a nice 1/2 stop for us"
Reviewed on Sep 19, 2025
Courtyard by Marriott Winchester
300 Marriott Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $116 total per night from Oct 5 to Oct 6
$116 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"Very clean and the employees hospitality was outstanding."
Reviewed on Sep 15, 2025
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
$91 nightly
The price is $99 total per night from Oct 26 to Oct 27
$99 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Nice hotel for a quick night stay. Front desk staff were super friendly. Very clean. Close to things to do. Would stay again."
Reviewed on Sep 18, 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Oct 5 to Oct 6
$84 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests ...
"Room was very clean and comfortable. Breakfast was basic but better than most I've been to recently. Very satisfied with the stay."
Reviewed on Sep 22, 2025
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Old Town Winchester Hotel Guide
Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.
Nowhere else can you find better deals on Old Town Winchester area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Old Town Winchester to find the perfect one to will fit your budget.
Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Old Town Winchester are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.
Recent Old Town Winchester hotel reviews by fellow wanderers
The George Washington Hotel, A Wyndham Grand Hotel
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!"
A verified traveler stayed at The George Washington Hotel, A Wyndham Grand Hotel
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