Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Winchester historic hotels

Fitness facility
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)
"Great breakfast. 24 hr coffee. Clean rooms. Pet friendly! Friendly front desk staff"
United States
Jolene
The price is ￥15,933
￥18,052 total
includes taxes & fees
Jan 18 - Jan 19
Hampton Inn Winchester-University/Mall Area
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Historic Bluemont Village Home
Bluemont
10.0 out of 10, Exceptional, (39)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
United States
Mary S.
The price is ￥24,680
￥67,081 total
includes taxes & fees
Jan 11 - Jan 12
Historic Bluemont Village Home
Exterior
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, (263)
"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 ￥128,959
￥279,440 total
includes taxes & fees
Jan 15 - Jan 16
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, (1005)
"Very nice stay! Beth at the front desk was warm and welcoming!"
United States
Tyler
The price is ￥12,978
￥16,011 total
includes taxes & fees
Jan 21 - Jan 22
Mimslyn Inn Historic Hotels Of America
Meeting facility
Airlie Hotel

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (335)
"Gorgeous grounds. Worth the visit. "
United States
mary lynne
The price is ￥23,387
￥29,013 total
includes taxes & fees
Jan 15 - Jan 16
Airlie Hotel
Smart TV, table tennis, 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.
Walk to Old Rag* hot tub* 360 mountain views
Exterior
❤️ 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, (68)
"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 ￥6,205
￥16,416 total
includes taxes & fees
Jan 19 - Jan 20
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds
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 ￥20,359
￥34,382 total
includes taxes & fees
Jan 11 - Jan 12
Best location! Baltimore Suite @ historic 1799 Inn
Outdoor dining
Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
9.8 out of 10, Exceptional, (60)
"Bill’s place was great. Everything was just as described, clean, and comfortable. Bill was very kind and helpful! Awesome stay!"
United States
Joanne R.
The price is ￥23,257
￥36,033 total
includes taxes & fees
Jan 11 - Jan 12
Historic 2-Bedroom in Old Town Warrenton, Virginia
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.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville
10.0 out of 10, Exceptional, (341)
"Everything was perfect for our stay. "
United States
Debbie O.
The price is ￥25,293
￥43,609 total
includes taxes & fees
Jan 13 - Jan 14
"Solitude" Secluded 1 BR Cabin Nestled in the Woods 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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Yes"
Ken 1-night trip
Posted 19 hours ago
Hampton Inn Martinsburg

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 family-friendly area.
What's the best hotel in Winchester to be near historical sites?
Based on our travel expertise, Secret Gardens Carriage House 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 Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed 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 76 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 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 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.