Find Historic Hotels in Winchester, VA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester Historic Hotels

Top Winchester Historic Hotels

Our top choices for Winchester historic hotels

Mimslyn Inn Historic Hotels Of America
Exterior

Mimslyn Inn Historic Hotels Of America

3.0 star property
9.0 out of 10, Wonderful, (1003)
"I had a great stay here! It's an old historic building near Luray Caverns and Shenandoah, and I enjoyed the pool and hot tub the night I arrived, and the room was very comfortable. "
The price is SAR 455
SAR 561 total
includes taxes & fees
4 Sep - 5 Sep
Mimslyn Inn Historic Hotels Of America
Airlie Hotel
Fireplace

Airlie Hotel

3.5 star property
8.8 out of 10, Excellent, (311)
"We love the old charm this hotel offers, while the rooms are cozy and new!"
The price is SAR 448
SAR 548 total
includes taxes & fees
3 Sep - 4 Sep
Airlie Hotel
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Pool

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

10.0 out of 10, Exceptional, (322)
"Loved the privacy "
The price is SAR 450
SAR 835 total
includes taxes & fees
21 Aug - 22 Aug
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (60)
"We truly loved this location and definitely will be back!"
The price is SAR 250
SAR 507 total
includes taxes & fees
1 Sep - 2 Sep
❤️ Secluded 1940s Romantic Tiny House on the River
The Creekside Cottage: Downtown | Pet-Friendly
Property grounds

The Creekside Cottage: Downtown | Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Great place to stay"
The price is SAR 867
SAR 1,406 total
includes taxes & fees
26 Aug - 27 Aug
The Creekside Cottage: Downtown | Pet-Friendly
Downtown: Explore Shepherdstown from cozy 1br apartment
TV

Downtown: Explore Shepherdstown from cozy 1br apartment

9.4 out of 10, Exceptional, (15)
"Perfect size, location and amenities."
The price is SAR 450
SAR 759 total
includes taxes & fees
25 Aug - 26 Aug
Downtown: Explore Shepherdstown from cozy 1br apartment
The Cottage on Royal - Historic Leesburg Home
Terrace/patio

The Cottage on Royal - Historic Leesburg Home

10.0 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay. The property was in a great location and was in excellent condition with all the amenities you needed to make your stay comfortable. I will definitely book this property again on my next visit!"
The Cottage on Royal - Historic Leesburg Home
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Property grounds

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (87)
"Great place that works well for Rixey Manor weddings "
The price is SAR 769
SAR 1,584 total
includes taxes & fees
7 Sep - 8 Sep
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Trouvaille House Suite 2 Parisian Apartment
Exterior detail

Trouvaille House Suite 2 Parisian Apartment

10.0 out of 10, Exceptional, (28)
"Had a lovely time. Very peaceful and clean."
The price is SAR 653
SAR 1,024 total
includes taxes & fees
21 Aug - 22 Aug
Trouvaille House Suite 2 Parisian Apartment
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Outdoor pool

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

9.8 out of 10, Exceptional, (34)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
The price is SAR 1,220
SAR 1,711 total
includes taxes & fees
21 Aug - 22 Aug
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
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.

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Hotel has a walking mall right around the corner. Beds and pillows are always comfortable. Has nightly entertainment on weekends onsite at the Bar/Restaurant. "
Melissa 1-night trip
Posted 19 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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, 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. If you're interested in local history, another option for your trip is Secret Gardens Carriage House.
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 76 hotel accommodations bookable on Expedia, including 3 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 Abram's Delight. Cultural venues include Bright Box Theater, Winchester Little Theater, and Museum of the Shenandoah Valley. 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.