Find Historic Hotels in Winchester, VA

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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

2.5 star property
Winchester
9.0 out of 10, Wonderful, (1000)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is SAR 372
SAR 422 total
includes taxes & fees
4 Jan - 5 January 2026
Hampton Inn Winchester-University/Mall Area
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Bluemont
10.0 out of 10, Exceptional, (39)
"No need to look any further! Beautiful, clean,historic home in a perfect location. Close to wineries, breweries, Shenandoah River, hiking and only 45 minutes from DC. The host was very accommodating and friendly as well. We would highly recommend this home for you and your family. "
United States
Brian and Allison W.
The price is SAR 591
SAR 1,607 total
includes taxes & fees
14 Dec - 15 Dec
Historic Bluemont Village Home
Exterior
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

3.0 star property
Luray
9.0 out of 10, Wonderful, (1003)
"Friendly staff and excellent maid service. Also very good breakfast menu."
United States
Richard
The price is SAR 342
SAR 422 total
includes taxes & fees
4 Jan - 5 January 2026
Mimslyn Inn Historic Hotels Of America
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
9.8 out of 10, Exceptional, (65)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is SAR 149
SAR 393 total
includes taxes & fees
16 Dec - 17 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds
Best location! The Iron Horse @ historic 1799 Inn

Best location! The Iron Horse @ historic 1799 Inn

Harpers Ferry
9.8 out of 10, Exceptional, (11)
"Perfect location, very nice accommodations! Loved the layout of the top apartment and loved the close proximity to many restaurants and trails. Would love to come back!"
United States
Anna S.
The price is SAR 525
SAR 970 total
includes taxes & fees
11 Dec - 12 Dec
Best location! The Iron Horse @ historic 1799 Inn
Exterior
Secluded,Mountain,View,Chalet,Hot tub,Wifi,King beds,Firepit,Near Cacapon Resort

Secluded,Mountain,View,Chalet,Hot tub,Wifi,King beds,Firepit,Near Cacapon Resort

Berkeley Springs
10.0 out of 10, Exceptional, (276)
"Beautiful view, peaceful surroundings with a house that has all the amenities and can make fun memories."
United States
Tracy K.
The price is SAR 661
SAR 2,305 total
includes taxes & fees
11 Dec - 12 Dec
Secluded,Mountain,View,Chalet,Hot tub,Wifi,King beds,Firepit,Near Cacapon Resort
Pool
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Rileyville
10.0 out of 10, Exceptional, (340)
"Excellent experience! The cabin was great, the location was great, the sights and people were great!"
United States
Tom A.
The price is SAR 465
SAR 857 total
includes taxes & fees
11 Dec - 12 Dec
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Outdoor spa tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Rileyville
10.0 out of 10, Exceptional, (350)
"We had a great time and can't wait to return"
United States
Jacqueline B.
The price is SAR 494
SAR 895 total
includes taxes & fees
15 Dec - 16 Dec
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Fireplace
Airlie Hotel

Airlie Hotel

3.5 star property
Warrenton
8.6 out of 10, Excellent, (331)
"Gorgeous grounds. Worth the visit. "
United States
mary lynne
The price is SAR 687
SAR 805 total
includes taxes & fees
23 Dec - 24 Dec
Airlie Hotel
Property grounds
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Rileyville
9.8 out of 10, Exceptional, (309)
"Absolutely adorable mountain cabin with perfect views and all the comforts of home. Loved the hot tub and the fire pit. Already looking forward to coming back again sometime."
United States
Marlo G.
The price is SAR 465
SAR 857 total
includes taxes & fees
11 Dec - 12 Dec
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 2 days ago
The George Washington Hotel, A Wyndham Grand Hotel

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Frequently asked questions

What should I expect on my historical trip to Winchester?
Visitors love the fascinating history they can explore on a trip to Winchester. The array of shops and top-notch restaurants are some of the places to visit while you're here. You can also discover the theater scene during your vacation in this vibrant area.
What's the best hotel in Winchester to be near historical sites?
Based on our travel expertise, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a top guesthouse on Expedia for those interested in history, and it features onsite laundry facilities and in-room kitchens. Patsy Cline Historic House is a short 4-minute drive away. A couple of other options to soak up the local history include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 79 hotel accommodations 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 Stonewall Jackson's Headquarters, Patsy Cline Historic House, and George Washington's Office. Cultural venues include Bright Box Theater, Museum of the Shenandoah Valley, and Old Court House Civil War Museum. A couple of additional sights to add to your agenda are Shenandoah Valley Discovery Museum and Apple Blossom Mall.
What is a historic hotel like in Winchester?
Guests who choose a historic hotel can stay someplace that has a national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel provided that it's of special interest. Traditional architecture and period features are often found in the public spaces and guestrooms of historic hotels in Winchester, giving a historical feel.
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 U.S., whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to place more significance on the building and architecture itself. Heritage hotels draw their meaning mainly from the cultural value and how it shaped the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, but hotel interiors are fitted with modern conveniences and safety features. Visitors should expect the popular amenities you'd get from a hotel such as private rooms with updated bathroom facilities, WiFi, and more. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's rundown or uncomfortable for guests.