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

Our top choices for Winchester historic hotels

Interior

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 AED 221
AED 588 total
includes taxes & fees
14 Jul - 15 Jul
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Terrace/patio

The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (21 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is AED 1,107
AED 2,047 total
includes taxes & fees
14 Jul - 15 Jul
The Cottage on Royal - Historic Leesburg Home
Meeting facility

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (351 reviews)
"What a lovely place to stay and visit. The grounds were beautiful and well-kept. The staff was great. The amenities were what you could expect at a much bigger resort property."
United States
Jason
The price is AED 769
AED 917 total
includes taxes & fees
14 Jul - 15 Jul
Airlie Hotel
Outdoor dining

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, (38 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is AED 1,286
AED 1,784 total
includes taxes & fees
14 Jul - 15 Jul
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (70 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is AED 1,194
AED 1,545 total
includes taxes & fees
14 Jul - 15 Jul
The Van Gogh Room in Villa
Smart TV, books, stereo

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Harpers Ferry
10.0 out of 10, Exceptional, (165 reviews)
"Everything was great! Would definitely recommend to anyone wanting to check out the area! Thanks again!! "
United States
Matt G.
The price is AED 771
AED 1,567 total
includes taxes & fees
19 Jul - 20 Jul
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
10.0 out of 10, Exceptional, (6 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 AED 909
AED 1,492 total
includes taxes & fees
14 Jul - 15 Jul
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Smart TV, fireplace, DVD player, books

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is AED 438
AED 1,477 total
includes taxes & fees
19 Jul - 20 Jul
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (113 reviews)
"The house was as advertised and served as a great location for our retreat! We had a freak plumbing emergency, and the host fixed it within literally an hour. "
United States
Connie V.
The price is AED 732
AED 2,188 total
includes taxes & fees
26 Jul - 27 Jul
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Outdoor spa tub

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Harpers Ferry
9.6 out of 10, Exceptional, (18 reviews)
"The house was clean and accommodating. It was truly right next door to the river riders establishment. The hot tub was AMAZING! Wish I had more time to enjoy it. We would definitely rent it again "
United States
Lynette M.
The price is AED 370
AED 1,389 total
includes taxes & fees
15 Jul - 16 Jul
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
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

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"My room was perfect, as always."
Alan 1-night trip
Posted 3 hours ago
Courtyard by Marriott Winchester

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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 family-friendly area.
What's the best hotel in Winchester to be near historical sites?
Based on our travel expertise, Secret Gardens Carriage House A 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. A couple of other options to soak up the local history include Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 78 hotel accommodations bookable on Expedia, including 4 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 Abram's Delight. Cultural venues include Winchester Little Theater, Museum of the Shenandoah Valley, and Bright Box Theater. 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.