Virginia may have travel restrictions in place due to COVID-19.

Find out moreOpens in new tab or window
Photo by Fernando Begay

Find Historic Hotels in Winchester, VA from $50

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Top Winchester Historic Hotels

The Ashby Inn & Restaurant
3.5 out of 5
692 Federal St, Paris, VA
Get Rates
4.7/5Exceptional! (41 reviews)

"Greater at the door as we were exiting our car. Taken on a brief tour of the facilities as we were shown our room. Great way to start our stay. Breakfast the next.morning was delicious. Our server paid just the right amount of attention as I waited for that first cup.of coffee to kick in. Just a ..."…"

Reviewed on Jun 28, 2019

The Ashby Inn & Restaurant
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
Get Rates
4.6/5Exceptional! (253 reviews)
Saturday stay

"Small room but was to be expected in a historic inn. Everyone of the staff we encountered were super nice and offered exceptional service. The group of locals at the bar were quite a collection of characters to say the least. But very friendly."…"

Reviewed on Mar 2, 2020

Wayside Inn
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $101 per night from Nov 29 to Nov 30
4.6/5Exceptional! (977 reviews)

""…"

Reviewed on Nov 5, 2020

The George Washington Hotel, A Wyndham Grand Hotel
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $84 per night from Nov 27 to Nov 28
4.6/5Wonderful! (1,196 reviews)

"I travel Spring and Fall and stay here using the pet friendly feature which I love."…"

Reviewed on Nov 2, 2020

Country Inn & Suites by Radisson, Winchester, VA
Holiday Inn Winchester Se-Historic Gateway
3 out of 5
333 Front Royal Pike, Winchester, VA
Free Cancellation
The price is $80 per night from Nov 29 to Nov 30
4.5/5Wonderful! (887 reviews)

"It was pristinely clean but we were there for only one night driving through and arrived late and left early so did not use amenities. The TV did not provide much though and was confusing to understand. No movies accept HBO"…"

Reviewed on Nov 23, 2020

Holiday Inn Winchester Se-Historic Gateway
Hampton Inn Winchester-University/Mall Area
2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $114 per night from Nov 27 to Nov 28
4.5/5Wonderful! (807 reviews)

"We have stayed here several times as our daughter attends Shenandoah University which is just across the street, so we love the convenience. While we appreciated the posted signs requiring face coverings, it was not enforced, leading to a few uncomfortable moments in elevators with uncovered ..."…"

Reviewed on Oct 12, 2020

Hampton Inn Winchester-University/Mall Area
Holiday Inn Express Hotel & Suites Winchester
2.5 out of 5
142 Foxridge Ln, Winchester, VA
Free Cancellation
The price is $85 per night from Dec 7 to Dec 8
4.5/5Wonderful! (468 reviews)

"Everything was nice and clean but the bed was god awful hard."…"

Reviewed on Oct 18, 2020

Holiday Inn Express Hotel & Suites Winchester
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
Free CancellationReserve now, pay when you stay
The price is $79 per night from Dec 20 to Dec 21
4.4/5Wonderful! (721 reviews)

"The staff made you feel comfortable even while following strict covid guidelines. The room was clean and comfortable. It was cool at night, and I wish I had been able to open the window a little more. There was plenty of coffee in the morning and a to-go breakfast (which I didn't take because I was ..."…"

Reviewed on Oct 13, 2020

Fairfield Inn & Suites Strasburg Shenandoah Valley
Hampton Inn Winchester N/Conference Center, VA
2.5 out of 5
1204 Berryville Avenue, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $114 per night from Nov 27 to Nov 28
4.4/5Excellent! (358 reviews)

"The faculty was very clean. The bed was comfortable. The staff was very nice!"…"

Reviewed on Aug 2, 2020

Hampton Inn Winchester N/Conference Center, VA
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $89 per night from Dec 23 to Dec 24
4.4/5Excellent! (986 reviews)

"This is a clean and comfortable hotel. We would stay again."…"

Reviewed on Nov 23, 2020

Wingate by Wyndham Winchester
Courtyard by Marriott Winchester
3 out of 5
300 Marriott Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $71 per night from Nov 27 to Nov 28
4.4/5Excellent! (524 reviews)

"Clean and convenient location. Staff was very professional and helpful."…"

Reviewed on Nov 6, 2020

Courtyard by Marriott Winchester
Quality Inn
2.5 out of 5
1601 Martinsburg Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $67 per night from Dec 7 to Dec 8
4.3/5Excellent! (552 reviews)

"Very clean, quiet, and orderly. Great staff, everything was great."…"

Reviewed on Oct 12, 2020

Quality Inn
Fairfield Inn & Suites Winchester
2.5 out of 5
250 Front Royal Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $67 per night from Dec 20 to Dec 21
4.2/5Excellent! (244 reviews)

"Bed was very comfortable and beautiful water pressure for shower. Said included breakfast yet when we got there was grab in go only due to COVID. i understand but site should of informed us."…"

Reviewed on Oct 27, 2020

Fairfield Inn & Suites Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $89 per night from Dec 3 to Dec 4
4.2/5Excellent! (973 reviews)

"It was quiet. Loved the decor and amenities. Very clean and comfortable. Pet friendly was a must have."…"

Reviewed on Oct 24, 2020

La Quinta Inn & Suites by Wyndham Winchester
Motel 6 Winchester, VA
2 out of 5
2951 Valley Avenue, Winchester, VA
Free Cancellation
The price is $50 per night from Dec 6 to Dec 7
4/5Very Good! (845 reviews)

"Beds could be a little more comfortable but it’s nice overall"…"

Reviewed on Oct 12, 2020

Motel 6 Winchester, VA
Hotel Strasburg
3 out of 5
213 S. Holliday Street, Strasburg, VA
Get Rates
3.9/5Good! (727 reviews)

"Great place, just wish Confederacy celebration was toned down"…"

Reviewed on Mar 17, 2020

Hotel Strasburg
Clarion Inn & Conference Center
2.5 out of 5
711 Millwood Ave, Winchester, VA
Get Rates
3.9/5Good! (956 reviews)

"Great location and staff... spacious and clean will definitely be back"…"

Reviewed on Nov 9, 2020

Clarion Inn & Conference Center
Red Roof Inn Winchester, VA
2 out of 5
991 Millwood Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $60 per night from Nov 29 to Nov 30
3.5/5Good! (990 reviews)

"Very friendly lady upfront debt help me and my boyfriend get through how to use our cash app"…"

Reviewed on Oct 21, 2020

Red Roof Inn Winchester, VA
Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 out of 5
10 S Commerce Ave, Front Royal, VA
Free CancellationReserve now, pay when you stay
The price is $53 per night from Dec 8 to Dec 9
3.2/5 (428 reviews)
kay for one night

"Hotel could use some renovating. Okay room for the money."…"

Reviewed on Aug 25, 2020

Baymont by Wyndham Front Royal Near Shenandoah National Park
Motel 6 Front Royal, VA
2 out of 5
141 West 15th Street, Front Royal, VA
Free Cancellation
The price is $51 per night from Dec 6 to Dec 7
3.2/5 (206 reviews)

"Being able to bring our small shi tuz along on vacation made vacation more enjoyable. Thanks to Motel 6 and their staff it made things much smoother. When visiting the area again I would not hesitate to stay here again."…"

Reviewed on Oct 19, 2020

Motel 6 Front Royal, VA
Don't see what you're looking for?
We've got more Historic Hotels. Find the right one for you.
View all properties
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.

Guide to Winchester Historic Hotels

Traveling to new places can be more than just highlighting a place on your map, it can also be about taking in the culture and history of a place. One of the best ways to experience the culture of a region is to absorb yourself in its history. Exploring the region's landmarks or museums is a great beginning, but staying in a Winchester historic hotel can ferry you back in time. Get ready to pack your suitcases (and no need for the time machine) as your Winchester historic hotel awaits.

Grab Your Place in History

When you pass through the lobby of your Winchester hotel, you'll be transported back in time. With their classic charm and fascinating histories, you'll love the look and feel of your one-of-a kind accommodation. Although these accommodations may be older, they have most of the up-to-date conveniences that allow you to wind down on your trip. You'll find your room furnished with a comfy bed, and just about everything you might need for a marvelous getaway.

Once you've spent time admiring the hotel's grounds, you can tour the famous landmarks and art museums to appreciate more of the region's culture. Of course, all this exploring will stimulate your appetite. Feel free to go through Expedia's 13139 guest reviews for recommendations from like-minded travelers to help make your Winchester visit that much better. You can also ask your hotels' front desk to show you where some of the popular areas to grab a cocktail or a meal in Winchester are.

Your Winchester Accommodation Is Waiting

Winchester has 110 vintage hotels that maintain the look and feel of another era. Some of these famous hotels are where prominent writers may have stayed. You're certain to find a place with all the in-room amenities and the rate you want. If you desire to stay in one of these Winchester vintage hotels, book soon, or you may miss your chance on one of these unique accommodations.

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, The George Washington Hotel, A Wyndham Grand Hotel is a top 3.5-star historic hotel bookable on Expedia and it offers a full-service spa. Patsy Cline Historic House is a short 12-minute walk away. A couple of other options to soak up the local history include Hotel Strasburg and Fairfield Inn & Suites Winchester.
How many historically relevant hotels will I find in Winchester?
In Winchester, you’ll find 110 hotel accommodations bookable on Expedia, including 38 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, Hupp’s Hill Civil War Park, and Bing Crosby Stadium. Cultural venues include Winchester Little Theater, Museum of the Shenandoah Valley, and Blue Ridge Arts Council and Gallery. Additionally, you’ll find Hollywood Casino at Charles Town Races in the area.
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.

Travelers Loved These Historic Hotels

More trip options