Find Historic Hotels in Winchester, VA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Historic Hotels

Top 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 AED 379
AED 429 total
includes taxes & fees
28 Nov - 29 Nov
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 AED 578
AED 1,572 total
includes taxes & fees
23 Nov - 24 Nov
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)
"Historic, great bar food and nice front desk staff"
United States
Christine
The price is AED 405
AED 500 total
includes taxes & fees
24 Nov - 25 Nov
Mimslyn Inn Historic Hotels Of America
Fireplace
Airlie Hotel

Airlie Hotel

3.5 star property
Warrenton
8.6 out of 10, Excellent, (330)
"Gorgeous grounds. Worth the visit. "
United States
mary lynne
The price is AED 610
AED 720 total
includes taxes & fees
26 Nov - 27 Nov
Airlie Hotel
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is AED 145
AED 385 total
includes taxes & fees
1 Dec - 2 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
Interior
Hot tub, Campfire ring and great location!

Hot tub, Campfire ring and great location!

Harpers Ferry
9.4 out of 10, Exceptional, (125)
"We had an amazing time in WV. The home was comfortable and met all of our needs. It was quiet and relaxing, but close to the major attractions for the action."
United States
Katrina P.
The price is AED 423
AED 1,440 total
includes taxes & fees
23 Nov - 24 Nov
Hot tub, Campfire ring and great location!
Smart TV
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 AED 477
AED 806 total
includes taxes & fees
23 Nov - 24 Nov
Best location! Baltimore Suite @ historic 1799 Inn
Outdoor spa tub
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Harpers Ferry
9.6 out of 10, Exceptional, (13)
"Nice property & nice location."
United States
Mary E.
The price is AED 423
AED 1,448 total
includes taxes & fees
23 Nov - 24 Nov
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
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, (337)
"Excellent experience! The cabin was great, the location was great, the sights and people were great!"
United States
Tom A.
The price is AED 523
AED 930 total
includes taxes & fees
25 Nov - 26 Nov
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Fridge, microwave, oven, stovetop
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry
9.8 out of 10, Exceptional, (105)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
United States
Debbie G.
The price is AED 570
AED 1,995 total
includes taxes & fees
24 Nov - 25 Nov
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
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

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Winchester Hotel Reviews

Motel 6 Winchester, VA

Motel 6 Winchester, VA

10/10 Excellent
"Great room at a great price. Front desk staff went above and beyond to make it a great stay."
James 1-night trip
Posted 3 days ago
Motel 6 Winchester, VA

Explore a world of travel with Expedia

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 Patsy Cline Historic House, Stonewall Jackson's Headquarters, 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.