Book the Best HISTORIC Hotels in Winchester 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 building with a maroon sign reading 'ANS INN & SUITES' indicating a hotel establishment.

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

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

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

Winchester

CA $85

CA $226 total

includes taxes & fees

Oct 27 - Oct 28

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.

CA $58

CA $151 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

3. Mimslyn Inn Historic Hotels Of America

Luray

Kenneth

CA $167

CA $206 total

includes taxes & fees

Nov 4 - Nov 5

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

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.

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

Raquel

CA $205

CA $256 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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

Rileyville

Heather R.

CA $237

CA $415 total

includes taxes & fees

Oct 22 - Oct 23

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

A wooden cabin with a porch, surrounded by trees.

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

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.

CA $276

CA $466 total

includes taxes & fees

Nov 12 - Nov 13

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

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.

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

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

The Plains

Jill M.

CA $349

CA $576 total

includes taxes & fees

Nov 1 - Nov 2

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

A grassy yard with trees and a stone wall.

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

Berkeley Spring

Karen O.

CA $339

CA $610 total

includes taxes & fees

Oct 28 - Oct 29

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Top Winchester Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"This hotel is worth the stay!"

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!"

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"👍😃 Great"

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."

Quality Inn Winchester

8/10 Good

"Breakfast was excellent. The staff are so friendly and helpful! We stay on our way to Fl. and are never disappointed."

Fairfield Inn & Suites by Marriott Winchester

8/10 Good

"It was great."

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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Room 1

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