The Best Historic Hotels in Winchester, VA from AED 392 in 2026

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Our top choices for Winchester historic hotels

A room with a dining table and chairs, a bed, and a kitchen area visible through an open doorway.

A compact kitchen with wooden cabinets, a microwave, a coffee maker, and a trash bin.

A building with a maroon sign reading 'ANS INN & SUITES' indicating a hotel establishment.

A compact kitchen with a sink, cabinets, and a microwave.

1. ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

Winchester

AED 221

AED 588 total

includes taxes & fees

20 Oct - 21 Oct

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

A circular fire pit surrounded by grass and small plants, with a bench and logs nearby.

A hammock hanging from a tree by a lake.

A room with a wooden table, two chairs, a small shelf with a pitcher and bowl, a framed picture, and a window with curtains.

2. ❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown

Dennis C.

AED 152

AED 392 total

includes taxes & fees

25 Oct - 26 Oct

A grand, two-story building with a symmetrical facade, large windows, and a central entrance with a decorative archway.

A formal dining area with multiple tables set for a meal, surrounded by elegant chairs and chandeliers.

A sunlit room with large windows, a tiled floor, and a seating area with a sofa and chairs.

A grand staircase with a red carpet, a wooden floor, and a chandelier.

3. Mimslyn Inn Historic Hotels Of America

Luray

Kenneth

AED 434

AED 535 total

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with a fireplace, two white sofas, a wooden coffee table, and a chandelier.

A large, two-story building with a symmetrical facade, a stone foundation, and a well-maintained lawn with flowering shrubs.

A spacious living room with a large beige sofa, a matching armchair, and a wooden coffee table. A chandelier hangs from the ceiling, and the room features large windows with blinds.

A large hall with high wooden ceilings and string lights, furnished with tables and chairs, and large windows offering views of greenery.

4. Airlie Hotel

Warrenton

Holly

AED 725

AED 870 total

includes taxes & fees

18 Nov - 19 Nov

A hot tub with a view of a snowy landscape and trees.

A room with a sliding glass door leading to an outdoor hot tub area, a wooden chair, and a wooden dresser.

A living room with a sofa, a wicker coffee table, and a bookshelf.

A living room with a fireplace, a television, a sofa, and a view of the outdoors.

5. "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Rileyville

Heather R.

AED 617

AED 1,071 total

includes taxes & fees

22 Oct - 23 Oct

A hot tub with a clear view of a forested area through the surrounding wooden deck.

A cozy living room with a beige sofa, a wooden coffee table, and a large window with curtains.

A room with a sliding glass door leading to an outdoor deck.

A wooden cabin with a porch, surrounded by trees.

6. "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Rileyville

Sarah L.

AED 716

AED 1,186 total

includes taxes & fees

12 Nov - 13 Nov

A two-story building with a garage entrance, surrounded by lush greenery and a stone wall.

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with red chairs and a glass table.

A stable with two horses and a house in the background.

A living room with a piano, a sofa, a coffee table, and a lamp.

7. Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

The Plains

Jill M.

AED 909

AED 1,460 total

includes taxes & fees

20 Oct - 21 Oct

A stone fire pit surrounded by stone benches in a grassy area with trees in the background.

A grassy yard with trees and a stone wall.

A two-story house with a stone facade, a balcony with a wooden railing, and a stone wall surrounding the property.

A living room with leather sofas, a coffee table, and a chandelier. There is a dining area in the background with a table and chairs.

8. Luxury And Beautiful House With Amazing Mountain View. Perfect For Getaway

Berkeley Spring

Karen O.

AED 882

AED 1,578 total

includes taxes & fees

20 Oct - 21 Oct

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Top Winchester Hotel Reviews

Quality Inn Harpers Ferry - Charles Town

8/10 Good

"Very clean and up to date. I felt very comfortable. Super easy parking. I do wish breakfast had a bit more variety. Also I could hear people talking in the next room most of the night."

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good

"The rooms were clean and the climate control was good. The staff were friendly. The property had a cheerful seasonal display to greet guests. The property needs updated carpets and room ameneties. Our refrigerator was old and in disrepair. There were patches on the walls in the bathroom that were not painted over. I have stayed many times over the years and have noticed that the service is great but the place is in the need of refreshing!"

Fairfield Inn & Suites by Marriott Winchester

8/10 Good

"It was great."

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"Location is excellent. Walking distance to restaurants, coffee shops and bars as well as historical sites. Staff is always excellent, neatly dressed, well spoken and professional. The property is an architectural gem. The lobby, bar and general interior details like the interior woodwork, floors, elevators and mail chutes are remarkable. Best shower ever! Go to Knead Bread for breakfast. It would be a standout in any major city."

Mimslyn Inn Historic Hotels Of America

8/10 Good

"Lovely spacious room, light and well-appointed. Comfortable king-sized bed. But couch and armchair were worn. Sleeper couch was unusable. The property is beautiful and historic but past its prime."

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, Delightful and Serene Hundred Year Old Sweet Space Among the Gardens 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 - A space to relax and get away from it all..

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 George Washington's Office. 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.

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Change your mind

Treat yourself

Be picky

Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

1. ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

2. ❤️ Secluded 1940s Romantic Tiny House on the River