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

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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.

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
The price is ￥9,497
￥25,213 total
includes taxes & fees
Oct 29 - Oct 30
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.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is ￥6,541
￥16,867 total
includes taxes & fees
Nov 8 - Nov 9
❤️ 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.

3. Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,011 reviews)
"What a beautiful place to stay! Great amenities and close proximity to the National Park. Can’t wait to stay again!"
United States
Heather
The price is ￥20,782
￥25,639 total
includes taxes & fees
Nov 5 - Nov 6
Mimslyn Inn Historic Hotels Of America
A hot tub with a clear view of a forested area through the surrounding wooden 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
10.0 out of 10, Exceptional, (388 reviews)
"Beautiful, clean cabin nestled in the woods….enjoyed our stay and looking forward to returning at some point."
United States
Sarah L.
The price is ￥26,305
￥46,179 total
includes taxes & fees
Nov 12 - Nov 13
"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.

5. Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (369 reviews)
"Great and peaceful stay"
United States
Raquel
The price is ￥22,632
￥28,235 total
includes taxes & fees
Nov 23 - Nov 24
Airlie Hotel
A two-story building with a garage entrance, surrounded by lush greenery and a stone wall.

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
9.0 out of 10, Wonderful, (7 reviews)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
United States
Jill M.
The price is ￥38,979
￥63,456 total
includes taxes & fees
Oct 29 - Oct 30
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
A swimming pool with a white pergola and red flowers in the foreground, surrounded by green trees and a clear blue sky.

7. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (73 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveler
The price is ￥55,122
￥71,457 total
includes taxes & fees
Oct 31 - Nov 1
The Van Gogh Room in Villa
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

8. 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
10.0 out of 10, Exceptional, (132 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is ￥26,301
￥45,331 total
includes taxes & fees
Nov 9 - Nov 10
The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
A two-story house with a front porch, a covered entryway, and a visible front yard.

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

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
9.8 out of 10, Exceptional, (91 reviews)
"The absolute nicest, cleanest Vrbo I have ever stayed at! Great communication from the host, the property did not disappoint. It was well stocked with everything needed. And very clear directions for using the property and a terrific folder with area information. Will return."
United States
Janet G.
The price is ￥37,325
￥76,617 total
includes taxes & fees
Nov 9 - Nov 10
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
A backyard with a wooden deck, a pool, and a white fence.

10. 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
9.8 out of 10, Exceptional, (39 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is ￥62,996
￥86,719 total
includes taxes & fees
Oct 31 - Nov 1
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"This is our favorite stop on our way home to NY from S Car! Friendly staff, comfortable bed, awesome shower, and breakfast before we hit the road. Easy on and off I-81. What more could we ask for ?!"
Colleen 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

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.