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

Tonight
7 Jun - 8 Jun
Tomorrow
8 Jun - 9 Jun
Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun

Top Winchester Historic Hotels

Wayside Inn
Serves dinner and happy hour

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (393)
"It was quaint and interesting, but beware if you don’t like the smell of antiques. I had to track down staff to check in and call the manager who frankly seemed a bit miffed that I called her. Staff member was friendly upon arrival. Water pressure in the shower was not great, although the room was clean."
The price is AED 355
AED 428 total
includes taxes & fees
9 Jun - 10 Jun
Wayside Inn
The George Washington Hotel, A Wyndham Grand Hotel
Bar (on property)

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1007)
"Perfect hotel in a great location!!!"
The price is AED 465
AED 527 total
includes taxes & fees
15 Jun - 16 Jun
The George Washington Hotel, A Wyndham Grand Hotel
Hotel Strasburg
Building design

Hotel Strasburg

3.0 star property
7.8 out of 10, Good, (731)
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
Hotel Strasburg
Fairfield Inn & Suites by Marriott Winchester
Exterior

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
9.0 out of 10, Wonderful, (725)
"Clean rooms and friendly staff."
The price is AED 356
AED 387 total
includes taxes & fees
10 Jun - 11 Jun
Fairfield Inn & Suites by Marriott Winchester
Red Roof Inn Winchester, VA
1 bedroom, desk, blackout drapes, free cribs/infant beds

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1004)
"Nice and close to sightseeing places."
The price is AED 257
AED 280 total
includes taxes & fees
9 Jun - 10 Jun
Red Roof Inn Winchester, VA
Hampton Inn Winchester N/Conference Center, VA
Snack bar

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (762)
"Very nice and new hotel great room and nice bathroom will stay there again when we come to visit my Son in Berryville"
The price is AED 403
AED 456 total
includes taxes & fees
15 Jun - 16 Jun
Hampton Inn Winchester N/Conference Center, VA
Motel 6 Front Royal, VA
Lobby

Motel 6 Front Royal, VA

2.0 star property
6.8 out of 10, (472)
"This is a great location! "
The price is AED 239
AED 266 total
includes taxes & fees
11 Jun - 12 Jun
Motel 6 Front Royal, VA
Clarion Inn & Conference Center
Restaurant

Clarion Inn & Conference Center

2.5 star property
7.8 out of 10, Good, (952)
"Great location and staff... spacious and clean will definitely be back "
Clarion Inn & Conference Center
Hampton Inn Winchester-University/Mall Area
Porch

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1000)
"I loved everything about this hotel mainly the cleanliness and comfort. The front desk staff was very friendly."
The price is AED 412
AED 467 total
includes taxes & fees
15 Jun - 16 Jun
Hampton Inn Winchester-University/Mall Area
Motel 6 Winchester, VA
Free WiFi, bed sheets

Motel 6 Winchester, VA

2.0 star property
8.2 out of 10, Very Good, (1000)
"Nice"
The price is AED 235
AED 266 total
includes taxes & fees
11 Jun - 12 Jun
Motel 6 Winchester, 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.

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. If you’re interested in local history, another option for your trip is Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed.
How many historically relevant hotels will I find in Winchester?
In Winchester, you’ll find 75 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 The Kernstown Battlefield. 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 Mt Hebron Cemetery.
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.