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

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Check availability on Winchester Historic Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

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

ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Winchester
AED 221
AED 588 total
includes taxes & fees
25 Oct - 26 Oct
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.
A hammock hanging from a tree by a lake.
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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
United States
Dennis C.
AED 152
AED 392 total
includes taxes & fees
1 Nov - 2 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
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 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.

3. Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
Luray
United States
Heather
AED 465
AED 574 total
includes taxes & fees
5 Nov - 6 Nov
Mimslyn Inn Historic Hotels Of America
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 cozy living room with a stone fireplace, wooden flooring, a sofa, a television, and large windows with curtains.
A room with a sliding glass door leading to an outdoor deck.

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

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville
United States
Sarah L.
AED 612
AED 1,074 total
includes taxes & fees
12 Nov - 13 Nov
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
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 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.

5. Airlie Hotel

Airlie Hotel
Warrenton
United States
Raquel
AED 526
AED 656 total
includes taxes & fees
23 Nov - 24 Nov
Airlie Hotel
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 stable with two horses and a house in the background.

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
United States
Jill M.
AED 909
AED 1,488 total
includes taxes & fees
28 Oct - 29 Oct
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.
A spacious living room with a large sofa, a coffee table, and a TV. There is a ceiling fan, a rug, and a painting on the wall.
A white door with a decorative glass panel, a small table with a lamp, and a textured wall.
A bedroom with a large bed, a chandelier, a painting, and a window with curtains.

7. The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi

The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
Washington
United States
Daniel R.
AED 588
AED 1,026 total
includes taxes & fees
2 Nov - 3 Nov
The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
A backyard with a wooden deck, a pool, and a white fence.
A pathway leading through a park with cherry blossom trees.
A large, two-story house with a well-maintained lawn and a wooden fence in the foreground.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a gazebo.

8. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
United States
Dennis G.
AED 1,469
AED 2,022 total
includes taxes & fees
26 Oct - 27 Oct
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
A swimming pool with a white pergola and red flowers in the foreground, surrounded by green trees and a clear blue sky.
A bedroom with a bed, a chair, a table, and a TV. There is a window with a view of the outdoors.
A pathway leading through a park with cherry blossom trees.
Two people seated at a table with a view of a sunset over a hilly landscape.

9. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
United States
Anonymous traveler
AED 1,286
AED 1,654 total
includes taxes & fees
25 Oct - 26 Oct
The Van Gogh Room in Villa
A two-story house with a front porch, a covered entryway, and a visible front yard.
A hallway with a wooden floor, a small wooden table with a lamp, a mirror, and a window with curtains.
A living room with a beige sofa, a grey armchair, a wooden coffee table, and a television.
A kitchen with granite countertops, stainless steel appliances, wooden cabinets, and a built-in dishwasher.

10. Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
United States
Janet G.
AED 871
AED 1,775 total
includes taxes & fees
25 Oct - 26 Oct
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
View all properties

Top Winchester Hotel Reviews

Skyland

Skyland

8/10 Good
"The trails on and around this location were excellent."
Kimberly 3-night trip
Posted 1 hour ago
Skyland
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Not a he most attentive staff but otherwise fine."
Eric 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Le lit était très confortable."
Linda 1-night trip
Posted 4 hours ago
Travelodge by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"I really enjoyed the property. Extremely convenient to downtown attractions while being relatively quiet and nice. Staff was very helpful, room was lovely and clean and the pool was gorgeous."
MARY 1-night trip
Posted 5 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

8/10 Good
"Ok stay, free breakfast was good ( just there for a transit)."
Maria 1-night trip
Posted 9 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley
Motel 6 Winchester, VA

Motel 6 Winchester, VA

10/10 Excellent
"Nice"
Allyn 3-night trip
Posted 4 days ago
Motel 6 Winchester, VA

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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