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Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

Porch
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1000)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is 2.609.654 ₫
2.956.737 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester-University/Mall Area
Exterior
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1007)
"Friendly staff and excellent maid service. Also very good breakfast menu."
United States
Richard
The price is 2.343.954 ₫
2.891.725 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Mimslyn Inn Historic Hotels Of America
Fireplace
Airlie Hotel

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (333)
"Gorgeous grounds. Worth the visit. "
United States
mary lynne
The price is 3.832.810 ₫
4.586.131 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Airlie Hotel
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 Winchester Hotel Reviews

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Frequently asked questions

What should a history buff expect from a stay in Winchester?
Visitors love the significant historical sites they discover on a trip to Winchester. The major shopping area and top-notch restaurants are some of the places to visit while you're here. You can also discover the theatre scene during your holiday to this family-friendly area.
How many historically relevant hotels are located in Winchester?
Winchester has 79 hotels bookable on Expedia, including 4 designated as historic hotels or close to historic sites.
What are the top historical sites and other places in Winchester?
Winchester is notable for landmarks like Patsy Cline Historic House, Stonewall Jackson's Headquarters and The Kernstown Battlefield. Cultural venues include Bright Box Theater, Museum of the Shenandoah Valley and Winchester Little Theater. A couple of additional sights to add to your itinerary are Shenandoah Valley Discovery Museum and Apple Blossom Mall.
What is a historic hotel like in Winchester?
By choosing a historic hotel, you can sleep in a place that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be considered a historic hotel provided that it's of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Winchester, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
These terms are similar. "Historic hotel" is more commonly used in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to emphasise the architecture and building. Mainly a heritage hotel draws meaning from the place's cultural value and how it influenced the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Visitors should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's uncomfortable for guests or rundown.