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

3.5 star property
9.2 out of 10, Wonderful, (388)
"This inn is absolutely amazing. Staff went above and beyond to ensure we were comfortable and our stay was memorable. We plan to come back very soon! "
The price is AED 359
AED 432 total
includes taxes & fees
19 May - 20 May
Wayside Inn

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1005)
"Loved our stay!"
The price is AED 438
AED 496 total
includes taxes & fees
26 May - 27 May
The George Washington Hotel, A Wyndham Grand Hotel

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

2.5 star property
9.0 out of 10, Wonderful, (717)
"Clean rooms and friendly staff."
The price is AED 356
AED 387 total
includes taxes & fees
18 May - 19 May
Fairfield Inn & Suites by Marriott Winchester

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1002)
"I loved staying here "
The price is AED 257
AED 280 total
includes taxes & fees
18 May - 19 May
Red Roof Inn Winchester, VA

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (754)
"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
1 Jun - 2 Jun
Hampton Inn Winchester N/Conference Center, VA

Motel 6 Front Royal, VA

2.0 star property
6.8 out of 10, (461)
"This is a great location! "
The price is AED 239
AED 266 total
includes taxes & fees
18 May - 19 May
Motel 6 Front Royal, VA

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

2.5 star property
9.0 out of 10, Wonderful, (1000)
"The property is attractive and the staff was excellent. "
The price is AED 412
AED 467 total
includes taxes & fees
8 Jun - 9 Jun
Hampton Inn Winchester-University/Mall Area

Motel 6 Winchester, VA

2.0 star property
8.2 out of 10, Very Good, (1000)
"Enjoyed our stay. Very convenient on our yearly trip South. I wish the refrigerator had a small freezer. Will stay here again."
The price is AED 235
AED 266 total
includes taxes & fees
18 May - 19 May
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, 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 Abram’s Delight. 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 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.