Winchester Hotel Guide - Historic Hotels in Winchester, Virginia

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Check availability on Winchester Historic Hotels

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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, (1001)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is €98
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn Winchester-University/Mall Area
Outdoor dining
Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool
bluemont
9.8 out of 10, Exceptional, (262)
"We had such a wonderful time at this gorgeous house! It was clean, comfortable, spacious and very relaxing. Our group had kids and adults of all ages and everyone had a fantastic time. The brewery next door is an added bonus, and we didn’t have any issues with noise or crowds. We will definitely stay here again."
United States
Laura D.
The price is €1,475
includes taxes & fees
15 Jan - 16 Jan 2026
Breathtaking View with an Indoor Pool
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, (1004)
"Beautiful historic hotel, suite was cosy and spacious, staff was very friendly, and southern Sunday brunch was great!"
United States
Boris
The price is €93
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 €161
includes taxes & fees
28 Dec - 29 Dec
Airlie Hotel
Smart TV, ping pong, books
Walk to Old Rag* hot tub* 360 mountain views

Walk to Old Rag* hot tub* 360 mountain views

Walk to Old Rag* hot tub* 360 mountain views
Sperryville
10.0 out of 10, Exceptional, (21)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is €527
includes taxes & fees
4 Jan - 5 Jan 2026
Walk to Old Rag* hot tub* 360 mountain views
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (66)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is €93
includes taxes & fees
5 Jan - 6 Jan 2026
❤️ Secluded 1940s Romantic Tiny House on the River
Smart TV
Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (11)
"Great location in Lower Harper's Ferry. We completely enjoyed our stay. Will definitely be staying again in the future."
United States
Andrew R.
The price is €191
includes taxes & fees
28 Dec - 29 Dec
Best location! Baltimore Suite @ historic 1799 Inn
Terrace/patio
The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (18)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is €413
includes taxes & fees
29 Dec - 30 Dec
The Cottage on Royal - Historic Leesburg Home
Exterior
Rural Home, Hot Tub, Campfire, Hardwood Floors

Rural Home, Hot Tub, Campfire, Hardwood Floors

Rural Home, Hot Tub, Campfire, Hardwood Floors
Harpers Ferry
9.4 out of 10, Exceptional, (79)
"The property and house are beautiful. Clean and great location near historic Harper’s Ferry. "
United States
David M.
The price is €452
includes taxes & fees
26 Dec - 27 Dec
Rural Home, Hot Tub, Campfire, Hardwood Floors
Terrace/patio
Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (44)
"We really enjoyed our stay here, the location is perfect for exploring Harpers Ferry, within walking distance to everything. The cottage is well equipped, clean and cozy, perfect for a couples get away, would book again if returning to HF. The owner was very communicated, had well organized info for the stay and was easy to work with"
United States
Brandon L.
The price is €236
includes taxes & fees
13 Jan - 14 Jan 2026
Enchanting Cottage, walk to Downtown Harpers Ferry
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Staff support was sufficient, Peter was kind and accommodating. The room was sparse with a giant empty space and a lamp planted in the middle of it. I don't know if there's not supposed to be a sofa in there but it looked awkward. The rooms are not soundproof as I could hear the renter in the room above me rolling around on the office chair and walking around"
Cara 1-night trip
Posted 2 days ago
Spark by Hilton Winchester

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.
What's the best accommodation in Winchester to absorb the local history?
Based on our travel expertise, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a top guest house on Expedia for those interested in history, and it features on-site laundry facilities and in-room kitchens. Patsy Cline Historic House is a short 4-minute drive away. A couple of other options near historic sites include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
How many historically relevant hotels are located in Winchester?
Winchester has 78 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.