Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Compare Winchester Historic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Wayside Inn
Serves dinner and happy hour

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (385)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"
The price is SAR 394
SAR 472 total
includes taxes & fees
11 Mar - 12 Mar
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, (1006)
"Solid, quiet building. Short convenient walk to old Town Winchester services. Reasonable, affordable room rates. Pleasant pool, hot tub and weight room. Customer-friendly staff. "
The price is SAR 475
SAR 538 total
includes taxes & fees
10 Mar - 11 Mar
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, (685)
"Great stay"
The price is SAR 347
SAR 378 total
includes taxes & fees
9 Mar - 10 Mar
Fairfield Inn & Suites by Marriott Winchester
Red Roof Inn Winchester, VA
Desk, blackout drapes, free cribs/infant beds, free WiFi

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1005)
"Quiet area"
The price is SAR 236
SAR 257 total
includes taxes & fees
8 Mar - 9 Mar
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, (733)
"Very clean hotel and every staff member was super friendly. Rooms were spotless and very quiet "
The price is SAR 395
SAR 448 total
includes taxes & fees
16 Mar - 17 Mar
Hampton Inn Winchester N/Conference Center, VA
Motel 6 Front Royal, VA
Lobby

Motel 6 Front Royal, VA

2.0 star property
6.6 out of 10, (441)
"Love the stay "
The price is SAR 244
SAR 271 total
includes taxes & fees
5 Mar - 6 Mar
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, (1003)
"Great stay for access to university."
The price is SAR 379
SAR 430 total
includes taxes & fees
16 Mar - 17 Mar
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)
"Was a good stay."
The price is SAR 232
SAR 263 total
includes taxes & fees
9 Mar - 10 Mar
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 family-friendly area.
What's the best hotel in Winchester to be near historical sites?
Based on our travel expertise, Find the secrets to peace and beauty here! is a top guesthouse for history buffs booking on Expedia and it features 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 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 The Kernstown Battlefield. 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 Jim Barnett Park.
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.