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

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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

A hotel room with a bed, a mirror, a kitchenette, and a door leading to another room.

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 compact kitchen with white cabinets, a sink, and a countertop with various kitchen items. There is a bed with a patterned bedspread and pillows, and a window with curtains.

A hammock hanging from a tree by a lake.

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

Shepherdstown

Dennis C.

AED 152

AED 392 total

includes taxes & fees

1 Nov - 2 Nov

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

A covered outdoor area with a fountain, benches, and a building with columns.

4. Airlie Hotel

Warrenton

Raquel

AED 533

AED 664 total

includes taxes & fees

15 Nov - 16 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 fireplace, a television, a sofa, and a view of the outdoors.

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

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

Rileyville

Heather R.

AED 617

AED 1,076 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 room with a sliding glass door leading to an outdoor deck.

A wooden cabin with a porch, surrounded by trees.

A cozy living room with a stone fireplace, wooden flooring, a sofa, a television, and large windows with curtains.

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.

An outdoor seating area with Adirondack chairs and a table, a covered grill, and a house with a porch.

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

The Plains

Jill M.

AED 909

AED 1,480 total

includes taxes & fees

21 Oct - 22 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 modern kitchen with stainless steel appliances, wooden cabinets, and a central island.

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

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

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Great service excellent staff"

Courtyard by Marriott Winchester

10/10 Excellent

"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."

Quality Inn Harpers Ferry - Charles Town

8/10 Good

"Clean room. Very close to Appalachian trail, close to park information center, shuttle service to lower town. NO elevator, so stairs were hard for us carrying luggage. Desk clerk helped which was wonderful. Being so close to everything & being able to have a 1st floor room. Would definitely stay their again. We r in r 80's. Stairs r hard , but managed parr of the trail"

Travelodge by Wyndham Winchester

8/10 Good

"Room was comfortable. Staff very helpful. Property was a bit shabby."

Fairfield Inn & Suites by Marriott Winchester

8/10 Good

"It was great."

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