Find Historic Hotels in Winchester, VA

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Pick from 40 Winchester Historic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Wayside Inn
Exterior

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (372)
"Love the inside. Rooms and public spaces were fantastic. Outside needs some rehab. "
The price is AED 386
AED 462 total
includes taxes & fees
26 Nov - 27 Nov
Wayside Inn
The George Washington Hotel, A Wyndham Grand Hotel
Exterior

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.2 out of 10, Wonderful, (1006)
"It’s very close to the local walking mall with stores and nice restaurants. parking was not a problem."
The price is AED 465
AED 527 total
includes taxes & fees
1 Dec - 2 Dec
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, (647)
"Great location. Friendly staff, very clean "
The price is AED 340
AED 370 total
includes taxes & fees
2 Dec - 3 Dec
Fairfield Inn & Suites by Marriott Winchester
Red Roof Inn Winchester, VA
Exterior

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1039)
"As described "
The price is AED 221
AED 241 total
includes taxes & fees
8 Dec - 9 Dec
Red Roof Inn Winchester, VA
Hampton Inn Winchester N/Conference Center, VA
Exterior

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (716)
"Would like it closer to restaurants"
The price is AED 393
AED 446 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Winchester N/Conference Center, VA
Motel 6 Front Royal, VA
Exterior

Motel 6 Front Royal, VA

2.0 star property
6.6 out of 10, (433)
"Awesome place "
The price is AED 239
AED 266 total
includes taxes & fees
26 Nov - 27 Nov
Motel 6 Front Royal, VA
Clarion Inn & Conference Center
Pool

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
Pool

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1015)
"The water was hot, it was clean, it was close to the highway, the bed was comfortable, the breakfast was great and finally the staff were professional friendly and helpful. What more can you ask for? The hotel is older but well looked after and clean. "
The price is AED 343
AED 389 total
includes taxes & fees
26 Dec - 27 Dec
Hampton Inn Winchester-University/Mall Area
Motel 6 Winchester, VA
Property entrance

Motel 6 Winchester, VA

2.0 star property
8.0 out of 10, Very Good, (1031)
"Best budget, pet friendly accommodation in our experience. Great staff. Clean. Quiet. Laundry facilities. "
The price is AED 228
AED 258 total
includes taxes & fees
27 Nov - 28 Nov
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.
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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 knowledge, 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.
How many historically relevant hotels will I find in Winchester?
In Winchester, you’ll find 74 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, Abram’s Delight, and The Kernstown Battlefield. Cultural venues include Museum of the Shenandoah Valley, Bright Box Theater, 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.