Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

Exterior

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,012 reviews)
"Lovely historic Inn."
United States
Karen
The price is AED 405
AED 500 total
includes taxes & fees
18 Jun - 19 Jun
Mimslyn Inn Historic Hotels Of America
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (77 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AED 264
AED 518 total
includes taxes & fees
6 Jul - 7 Jul
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
9.8 out of 10, Exceptional, (326 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is AED 573
AED 1,021 total
includes taxes & fees
18 Jun - 19 Jun
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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, (107 reviews)
"The house was beyond expectations."
United States
Eddie J.
The price is AED 409
AED 1,452 total
includes taxes & fees
15 Jun - 16 Jun
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Pool

"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, (361 reviews)
"Fantastic stay! Will definitely come back!"
United States
Tristan T.
The price is AED 609
AED 1,066 total
includes taxes & fees
21 Jun - 22 Jun
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Outdoor spa tub

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

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville
10.0 out of 10, Exceptional, (366 reviews)
"It was exactly what we needed, out of the way and in nature, but close to beautiful attractions and grocery stores "
United States
Aaron A.
The price is AED 735
AED 1,211 total
includes taxes & fees
12 Jul - 13 Jul
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
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, (111 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 499
AED 1,920 total
includes taxes & fees
15 Jun - 16 Jun
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Smart TV, table tennis, books

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (22 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is AED 944
AED 2,080 total
includes taxes & fees
15 Jun - 16 Jun
Walk to Old Rag | Hot Tub | Mountain Farmhouse
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 1,537 total
includes taxes & fees
15 Jun - 16 Jun
The Van Gogh Room in Villa
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, (37 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is AED 1,286
AED 1,771 total
includes taxes & fees
15 Jun - 16 Jun
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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Good job clean room comfortable and was easy in and out No breakfast options for gluten free"
Terry 1-night trip
Posted 1 hour ago
Travelodge by Wyndham 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 vibrant area.
What's the best hotel in Winchester to be near historical sites?
Based on our travel expertise, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed 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 Secret Gardens Carriage House 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 76 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, George Washington's Office, and Stonewall Jackson's Headquarters. Cultural venues include Bright Box Theater, Winchester Little Theater, and Museum of the Shenandoah Valley. A couple of additional sights to add to your agenda are Shenandoah Valley Discovery Museum and Jim Barnett Park.
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.