Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Tonight
7 Feb - 8 Feb
Tomorrow
8 Feb - 9 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 AED 579
AED 1,585 total
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 AED 308
AED 380 total
includes taxes & fees
15 Feb - 16 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 AED 548
AED 680 total
includes taxes & fees
8 Feb - 9 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 AED 145
AED 385 total
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 AED 544
AED 983 total
includes taxes & fees
8 Feb - 9 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 AED 612
AED 1,074 total
includes taxes & fees
18 Feb - 19 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 AED 544
AED 983 total
includes taxes & fees
8 Feb - 9 Feb
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Smart TV, table tennis, books

Walk to Old Rag* hot tub* 360 mountain views

Walk to Old Rag* hot tub* 360 mountain views
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 AED 955
AED 2,185 total
includes taxes & fees
8 Feb - 9 Feb
Walk to Old Rag* hot tub* 360 mountain views
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 AED 753
AED 1,551 total
includes taxes & fees
21 Feb - 22 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 AED 909
AED 1,468 total
includes taxes & fees
9 Feb - 10 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.
View all properties

Top Winchester Hotel Reviews

Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"Room was awesome, amazing experiences at the resort and really great customer service"
Anwar 2-night trip
Posted 3 weeks ago
Salamander Resort And Spa

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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 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 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 will I find in Winchester?
In Winchester, you'll find 77 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 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 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.