Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Tonight
5 Feb - 6 Feb
Tomorrow
6 Feb - 7 Feb
This weekend
7 Feb - 9 Feb
Next weekend
14 Feb - 16 Feb

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, (384)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"
The price is AED 275
AED 341 total
includes taxes & fees
7 Feb - 8 Feb
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)
"Very friendly, helpful staff! Live music at the bar!"
The price is AED 434
AED 492 total
includes taxes & fees
16 Feb - 17 Feb
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, (677)
" • Friendly & efficient staff • Great Breakfast • Extremely clean • lovely amenities "
The price is AED 340
AED 370 total
includes taxes & fees
8 Feb - 9 Feb
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)
"Quiet area"
The price is AED 225
AED 245 total
includes taxes & fees
16 Feb - 17 Feb
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, (730)
"We only reserved a room here because it was half way to our destination and we needed an overnight stay. We were sorry we could only stay one night! I have to say I think this was the cleanest hotel I’ve ever stayed in! The lobby was immaculate and we watch a woman cleaning it during breakfast…it was obvious she CARED about her job which explained why it was so nice. Breakfast was awesome, well done, Finally, the staff was so friendly and helpful!!! Both the check in and check out staff...
The price is AED 403
AED 456 total
includes taxes & fees
12 Feb - 13 Feb
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, (440)
"Love the stay "
The price is AED 220
AED 245 total
includes taxes & fees
12 Feb - 13 Feb
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, (1002)
"Quiet"
The price is AED 356
AED 403 total
includes taxes & fees
16 Feb - 17 Feb
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)
"Was a good stay."
The price is AED 228
AED 258 total
includes taxes & fees
16 Feb - 17 Feb
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 expertise, Find the secrets to peace and beauty here! is a top guesthouse on Expedia for those interested in history, and it features a spa tub and in-room kitchens. The Kernstown Battlefield is a short 3-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 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, The Kernstown Battlefield, and George Washington’s Office. 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.