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 a sink, cabinets, and a microwave.

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

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

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

Winchester

AED 221

AED 588 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

1 Nov - 2 Nov

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

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

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

A bar with a variety of liquor bottles and a stained glass window.

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

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

4. Airlie Hotel

Warrenton

Raquel

AED 533

AED 664 total

includes taxes & fees

22 Nov - 23 Nov

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

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

A rustic cabin with a porch, surrounded by a well-maintained lawn and trees.

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.

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

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

A wooden cabin with a porch, surrounded by trees.

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

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

Rileyville

Sarah L.

AED 612

AED 1,074 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.

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

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 1,488 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

A grassy yard with trees and a stone wall.

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

Berkeley Spring

Donald

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Top Winchester Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Front desk upgraded our room so we could fit our bikes in the room. Bed was too soft. Otherwise room was nice. Breakfast was good."

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Great room, attentive staff, breakfast hit all the notes"

Mimslyn Inn Historic Hotels Of America

10/10 Excellent

"The Speakeasy restaurant was excellent!"

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent

"Five stars all the way. The property was very well maintained and extremely clean. There was great water pressure in the shower. The staff was very attentive to our needs, and very friendly. I would definitely recommend this property!"

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"

Travelodge by Wyndham Winchester

10/10 Excellent

"Clean friendly"

Spark by Hilton Winchester

10/10 Excellent

"What a pleasure staying a night in such a new, sparkling clean hotel! Location was fantastic with lots of stores and restaurants and the Highway very close! Our room was extremely clean and comfy! The front desk clerk on the night of Oct 18 was fantastic and friendly! Breakfast was just Continental, but better than nothing!"

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."

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