Search Historic Hotels in Old Town Winchester

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Check availability on Old Town Winchester Historic Hotels

Tonight
7 Dec - 8 Dec
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8 Dec - 9 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

Top Old Town Winchester Historic Hotels

Porch
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is ₹8,927
₹10,115 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester-University/Mall Area
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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Top Old Town Winchester Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Everything was great, including breakfast "
Kevin 1-night trip
Posted 1 day ago
Quality Inn Winchester

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Frequently asked questions

What should I expect on my historical trip to Old Town Winchester?
Visitors in search of a tour of historical sites will want to plan a trip to Old Town Winchester. While you're here, be sure to check out the shops and live music. And also relish a stop at the top-notch restaurants in this walkable area.
How many historically relevant hotels will I find in Old Town Winchester?
Old Town Winchester is home to 12 hotels and other accommodation options bookable on Expedia though you won't find many designated historic hotels.
What are the top historical places and other sights to visit in Old Town Winchester?
Old Town Winchester is notable for landmarks like George Washington's Office. Cultural venues include Bright Box Theater and Old Court House Civil War Museum. A couple of additional sights to add to your itinerary are Shenandoah Valley Discovery Museum and Handley Regional Library.
What is a historic hotel like in Old Town Winchester?
Historic hotels give guests the opportunity to stay in a place that's been officially recognised with a historic designation. Historic hotels throughout the world can take the form of castles, palaces or even pubs or old police stations — as long as it's of special interest. These types of hotels in Old Town Winchester typically retain original qualities such as period features or traditional architecture within the guestrooms or public spaces.
What is the difference between a historic hotel and a heritage hotel?
They are quite similar. "Historic hotel" is a term often used in the US, whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to place more significance on the architecture and actual building. Heritage hotels draw their meaning mainly from the cultural value and how it inspired the community.
Do historic hotels in Old Town Winchester have modern facilities?
Yes, efforts are made to preserve the historic aspects and traditions, but interiors include modern conveniences and safety features. Tourists who book a stay can expect the amenities you'd find in a hotel such as Smart TVs, WiFi and updated bathroom facilities. Booking a historic hotel in Old Town Winchester doesn't mean you're choosing a place that's uncomfortable for guests or rundown.