Historic Hotels & Resorts in Winchester

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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, (1,008 reviews)
"Lovely historic Inn."
United States
Karen
The price is NZ$229
includes taxes & fees
21 June - 22 June
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 NZ$243
includes taxes & fees
29 June - 30 June
❤️ Secluded 1940s Romantic Tiny House on the River
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, (360 reviews)
"Wonderful getaway!"
United States
Samantha T.
The price is NZ$512
includes taxes & fees
25 June - 26 June
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
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 NZ$515
includes taxes & fees
25 June - 26 June
"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 NZ$688
includes taxes & fees
15 June - 16 June
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.2 out of 10, Wonderful, (71 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is NZ$720
includes taxes & fees
10 June - 11 June
The Van Gogh Room in Villa
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 NZ$907
includes taxes & fees
15 June - 16 June
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Smart TV, ping pong, books

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (21 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is NZ$1,016
includes taxes & fees
14 June - 15 June
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Property grounds

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, (90 reviews)
"Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is."
United States
Lisa S.
The price is NZ$750
includes taxes & fees
10 June - 11 June
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
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 NZ$830
includes taxes & fees
10 June - 11 June
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Really nice motel! Very clean, inside & out. Room was very large. Breakfast was a pleasant surprise- several hot items & staff member there refilling items all the time."
Sharon 3-night trip
Posted 12 hours ago
Quality Inn Winchester

Frequently asked questions

What should a history buff expect from a stay in Winchester?
Visitors love the significant historical sites they discover on a trip to Winchester. The major shopping area and top-notch restaurants are some of the places to visit while you're here. You can also discover the theatre scene during your holiday to this vibrant area.
What's the best accommodation in Winchester to absorb the local history?
Based on our travel expertise, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a top guest house on Expedia for those interested in history, and it features on-site laundry facilities and in-room kitchens. Patsy Cline Historic House is a short 4-minute drive away. A couple of other options near historic sites include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
How many historically relevant hotels are located in Winchester?
Winchester has 76 hotels 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 itinerary are Shenandoah Valley Discovery Museum and Jim Barnett Park.
What is a historic hotel like in Winchester?
By choosing a historic hotel, you can sleep in a place that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be considered a historic hotel provided that it's of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Winchester, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
These terms are similar. "Historic hotel" is more commonly used in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to emphasise the architecture and building. Mainly a heritage hotel draws meaning from the place's cultural value and how it influenced the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Visitors should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's uncomfortable for guests or rundown.