Find Historic Hotels in Winchester, VA

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Compare Winchester Historic Hotels 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, (376)
"Love the inside. Rooms and public spaces were fantastic. Outside needs some rehab. "
The price is AED 275
AED 341 total
includes taxes & fees
28 Dec - 29 Dec
Wayside Inn
The George Washington Hotel, A Wyndham Grand Hotel
Exterior

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1005)
"Lovely stay, staff were kind and helpful, parking was easy and plenty of cool places to dine within walking distance. We love coming here. "
The price is AED 465
AED 527 total
includes taxes & fees
2 Jan - 3 January 2025
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, (661)
"I love the Christmas lights you have outside the building. Very welcoming! Beautiful place, immaculately C lean, great staff!"
The price is AED 340
AED 370 total
includes taxes & fees
29 Dec - 30 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, (1001)
"Nice, clean, easy"
The price is AED 218
AED 237 total
includes taxes & fees
7 Jan - 8 January 2025
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, (724)
"Cleanest Hampton Inn I have ever stayed at. Staff was warm and welcoming. Breakfast had lots of options. Definitely will stay again. "
The price is AED 393
AED 446 total
includes taxes & fees
2 Jan - 3 January 2025
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, (436)
"Love going there. Staff are amazing people. "
The price is AED 239
AED 266 total
includes taxes & fees
29 Dec - 30 Dec
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, (1000)
"This was a great hotel to visit the University right across the street. The hotel was nicely updated and it had a friendly staff. We will be back!"
The price is AED 356
AED 403 total
includes taxes & fees
12 Jan - 13 January 2025
Hampton Inn Winchester-University/Mall Area
Motel 6 Winchester, VA
Property entrance

Motel 6 Winchester, VA

2.0 star property
8.2 out of 10, Very Good, (1000)
"Staff was extremely helpful and professional, I'm really enjoying my stay"
The price is AED 228
AED 258 total
includes taxes & fees
30 Dec - 31 Dec
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, 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 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.