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Search Historic Hotels in Winchester

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Top Winchester Historic Hotels

The Ashby Inn & Restaurant
3.5 out of 5
692 Federal St, Paris, VA
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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 28 Jun 2019

The Ashby Inn & Restaurant
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
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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 2 Mar 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 £84 per night from 1 Nov to 2 Nov
4.6/5Exceptional! (978 reviews)

"Great location and amenities. Room with jacuzzi was wonderful!"…"

Reviewed on 10 Oct 2020

The George Washington Hotel, A Wyndham Grand Hotel

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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 £70 per night from 23 Nov to 24 Nov
4.6/5Wonderful! (1,207 reviews)

"Staff was very nice, helpful. The room was good. There were some things in our bathroom that needed som TLC, but otherwise everything was good."…"

Reviewed on 21 Oct 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 £63 per night from 5 Nov to 6 Nov
4.5/5Wonderful! (877 reviews)

"When we arrived home, we realized our son left his taggie and teddy bear in the room. We called and the staff found it. They made him so happy that they took care of them until I went back to pick them up!"…"

Reviewed on 9 Oct 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 £97 per night from 27 Oct to 28 Oct
4.5/5Wonderful! (802 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 12 Oct 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 £79 per night from 17 Nov to 18 Nov
4.5/5Wonderful! (468 reviews)

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

Reviewed on 18 Oct 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 £84 per night from 27 Oct to 28 Oct
4.4/5Wonderful! (717 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 13 Oct 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 £97 per night from 27 Oct to 28 Oct
4.4/5Excellent! (354 reviews)

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

Reviewed on 2 Aug 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 £65 per night from 1 Nov to 2 Nov
4.4/5Excellent! (988 reviews)

"I have always chosen to stay here. This time, the hair dryer wouldn't turn on. The freezer thawed my icecream, si i set the thermostat to be colder. The ice cream still wouldn't completely freeze, but the veggies in the fridge part did freeze. The staff was wonderful, as usual."…"

Reviewed on 15 Sep 2020

Wingate by Wyndham Winchester
Quality Inn
2.5 out of 5
1601 Martinsburg Pike, Winchester, VA
Free cancellationReserve now, pay when you stay
The price is £60 per night from 1 Nov to 2 Nov
4.3/5Excellent! (552 reviews)

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

Reviewed on 12 Oct 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 £59 per night from 1 Nov to 2 Nov
4.2/5Excellent! (227 reviews)

"Seemed clean. As an older hotel it could use a little sprucing up. The bathroom door was warped so it couldn’t be closed all the way."…"

Reviewed on 12 Oct 2020

Fairfield Inn & Suites Winchester
Motel 6 Winchester, VA
2 out of 5
2951 Valley Avenue, Winchester, VA
Free cancellation
The price is £43 per night from 10 Nov to 11 Nov
4/5Very Good! (832 reviews)

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

Reviewed on 12 Oct 2020

Motel 6 Winchester, VA
Hotel Strasburg
3 out of 5
213 S. Holliday Street, Strasburg, VA
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3.9/5Good! (726 reviews)

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

Reviewed on 17 Mar 2020

Hotel Strasburg
Clarion Inn & Conference Center
2.5 out of 5
711 Millwood Ave, Winchester, VA
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3.9/5Good! (955 reviews)

"AC unit is extremely loud and doors take some wiggling to get them to lock properly."…"

Reviewed on 30 Jun 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 £54 per night from 27 Oct to 28 Oct
3.5/5Good! (991 reviews)

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

Reviewed on 21 Oct 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 £45 per night from 19 Nov to 20 Nov
3.3/5 (424 reviews)

"Currently still under renovation, however the room was clean. Check in was a little tough and I was charged 2x but was refunded for one. To go breakfast was apples, old oatmeal and untoasted"…"

Reviewed on 26 Jul 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 £50 per night from 22 Nov to 23 Nov
3.2/5 (203 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 19 Oct 2020

Motel 6 Front Royal, VA
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Your Guide to Historic Hotels in Winchester

When you take a Winchester trip out of town, it is easy to pick a modern hotel, or a chain you are familiar with. You know that your rooms will have all the standard amenities. But sometimes opting to stay in a more distinguished location can elevate your trip. Staying in a Winchester historic hotel still provides you with a well-appointed room that is also teeming with personality. Additionally, it allows you to immerse yourself in Winchester's past.

Old-World Charm, New World Amenities

When you pass through your Winchester hotel's lobby, you'll be transported back in time. With their old-world charm and mesmerising histories, you'll love how these historic hotels stand apart from their contemporary counterparts. While these hotels may be older, they have many of the up-to-date comforts that allow you to wind down during your stay. You will notice rooms outfitted with a cosy bed, lots of character, and about anything else you'll need for a wonderful stay.

After you have checked-in and had time to look around the historic hotel's grounds, you can continue to take in this culturally-rich area by exploring the famous landmarks and art museums. Of course, all this time travelling is going to stimulate your appetite. Feel free to check out our 11595 guest reviews for recommendations from fellow travellers to help make your Winchester visit great. You can also ask your hotels' front desk to recommend where a couple of the popular spots to enjoy a cocktail or tea in Winchester are.

Your Winchester Accommodation Is Waiting

Winchester has 40 vintage hotels that possess the look and feel of another era. Some of these famous lodgings may have been where notable actors stayed. You're sure to book a room possessing all the amenities and the characteristics you desire. If you are wishing 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 a history buff expect from a stay in Winchester?
Visitors love the significant historical sites they discover on a trip to Winchester. The major shopping area and top-notch restaurants are some of the places to visit while you’re here. You can also discover the theatre scene during your holiday to this family-friendly area.
What's the best accommodation in Winchester to absorb the local history?
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 near historic sites include Hotel Strasburg and Fairfield Inn & Suites Winchester.
How many historically relevant hotels are located in Winchester?
Winchester has 109 hotels bookable on Expedia, including 36 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?
By choosing a historic hotel, you can sleep in a place that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be considered a historic hotel provided that it’s of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Winchester, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
These terms are similar. “Historic hotel” is more commonly used in the U.S., while “heritage hotel” is often used in Asia and Europe. Historic hotels tend to emphasise the architecture and building. Mainly a heritage hotel draws meaning from the place’s cultural value and how it influenced the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Visitors should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn’t mean you will stay in a place that’s uncomfortable for guests or rundown.

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