Winchester Hotel Guide - Historic Hotels in Winchester, Virginia

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Check availability on Winchester Historic Hotels

Tonight
8 Feb - 9 Feb
Tomorrow
9 Feb - 10 Feb
Next weekend
13 Feb - 15 Feb
In two weeks
20 Feb - 22 Feb

Our top choices for Winchester historic hotels

Terrace/patio

Historic Bluemont Village Home

Historic Bluemont Village Home
Bluemont
10.0 out of 10, Exceptional, (39 reviews)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
United States
Mary S.
The price is €366
includes taxes & fees
9 Feb - 10 Feb
Historic Bluemont Village Home
Exterior

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,003 reviews)
"Perfect stay will stay again."
United States
EDWARD
The price is €93
includes taxes & fees
9 Feb - 10 Feb
Mimslyn Inn Historic Hotels Of America
Meeting facility

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (340 reviews)
"The HVAC system was right outside our room and was humming all night. Everything was comfortable but our sleep was extremely disrupted."
United States
Adam
The price is €157
includes taxes & fees
9 Feb - 10 Feb
Airlie Hotel
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (71 reviews)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is €93
includes taxes & fees
16 Feb - 17 Feb
❤️ 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, (345 reviews)
"Everything was perfect for our stay. "
United States
Debbie O.
The price is €229
includes taxes & fees
9 Feb - 10 Feb
"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, (355 reviews)
"Great place!"
United States
Donald C.
The price is €229
includes taxes & fees
9 Feb - 10 Feb
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
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, (313 reviews)
"Love our stay. Beautiful place. Scenic views were the best. "
United States
Joyce F.
The price is €229
includes taxes & fees
9 Feb - 10 Feb
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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 €504
includes taxes & fees
9 Feb - 10 Feb
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, (89 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 €355
includes taxes & fees
10 Feb - 11 Feb
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
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)
"The hosts are amazing! So accommodating and welcoming. The place is something special. "
United States
AMY B.
The price is €342
includes taxes & fees
18 Feb - 19 Feb
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
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

10/10 Excellent
"Room was great and breakfast was ok but had waffles"
Dennis 1-night trip
Posted 6 days ago
Travelodge 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 ANS Inn has clean, spacious rooms located on 5 acres with little traffic. and Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed.
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, Stonewall Jackson's Headquarters and The 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 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.