Historic Hotels & Resorts in Winchester from AU$153

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Check availability on Winchester Historic Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Best 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 AU$170
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester-University/Mall Area
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Bluemont
10.0 out of 10, Exceptional, (37)
"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 AU$655
includes taxes & fees
7 Dec - 8 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, (1009)
"Friendly staff and excellent maid service. Also very good breakfast menu."
United States
Richard
The price is AU$153
includes taxes & fees
1 Jan - 2 Jan 2026
Mimslyn Inn Historic Hotels Of America
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 AU$297
includes taxes & fees
11 Dec - 12 Dec
Airlie Hotel
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 AU$162
includes taxes & fees
16 Dec - 17 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
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 AU$334
includes taxes & fees
8 Dec - 9 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, (349)
"We had a great time and can't wait to return"
United States
Jacqueline B.
The price is AU$328
includes taxes & fees
8 Dec - 9 Dec
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
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 AU$395
includes taxes & fees
18 Dec - 19 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 AU$947
includes taxes & fees
10 Dec - 11 Dec
Secluded,Mountain,View,Chalet,Hot tub,Wifi,King beds,Firepit,Near Cacapon Resort
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, (308)
"We really enjoyed our stay! The Chalet was peaceful, clean, and perfect in every way. We enjoyed the hot tub and the view.Location was perfect, near Luray caverns and Shenandoah Park.Thank you for allowing us to stay there. It was a wonderful getaway."
United States
Amy A.
The price is AU$334
includes taxes & fees
8 Dec - 9 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.
View all properties

Top Winchester Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"good"
bhagavathgeet 1-night trip
Posted 4 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 vibrant 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 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 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 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.