Winchester Hotel Guide - Historic Hotels in Winchester, Virginia

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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, (1,014 reviews)
"we enjoyed a meal in the bar the grounds were gorgeous fine historic property"
United States
Barbara
The price is €93
includes taxes & fees
11 May - 12 May
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, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is €120
includes taxes & fees
21 May - 22 May
❤️ Secluded 1940s Romantic Tiny House on the River
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, (360 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 €233
includes taxes & fees
14 May - 15 May
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
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, (357 reviews)
"Wonderful getaway!"
United States
Samantha T.
The price is €238
includes taxes & fees
17 May - 18 May
"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, (322 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is €243
includes taxes & fees
21 May - 22 May
"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, (106 reviews)
"The house was beyond expectations."
United States
Eddie J.
The price is €433
includes taxes & fees
15 May - 16 May
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, (108 reviews)
"Laura was extremely helpful as we sorted out what we needed. Amazing location near Harpers Ferry and tons of fun stuff to do right there within shouting distance of the property."
United States
Steve Y.
The price is €469
includes taxes & fees
8 Jun - 9 Jun
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (69 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is €360
includes taxes & fees
11 May - 12 May
The Van Gogh Room in Villa
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 €373
includes taxes & fees
11 May - 12 May
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
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 €498
includes taxes & fees
11 May - 12 May
Walk to Old Rag | Hot Tub | Mountain Farmhouse
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

8/10 Good
"Bed was extremely comfortable. Linens were clean and of good quality. Breakfast area was clean, well stocked and attended to. Only one staff member during weekend evening but worked hard to satisfy my issue with non-working remote. Should have been spare or extra remotes at front desk. Hall carpeting needs to be replaced."
Anna 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham 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 family-friendly area.
What's the best accommodation in Winchester to absorb the local history?
Based on our travel expertise, Secret Gardens Carriage House 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 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 are located in Winchester?
Winchester has 78 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, Stonewall Jackson's Headquarters and Kernstown Battlefield. Cultural venues include Bright Box Theater, Museum of the Shenandoah Valley and Winchester Little Theater. A couple of additional sights to add to your itinerary are Shenandoah Valley Discovery Museum and Apple Blossom Mall.
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.