Find Historic Hotels in Winchester, VA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Historic Hotels

Tonight
25 Apr - 26 Apr
Tomorrow
26 Apr - 27 Apr
Next weekend
1 May - 3 May
In two weeks
8 May - 10 May

Our top choices for Winchester historic hotels

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (73 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
11 May - 12 May
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,000 reviews)
"Very nice property and nice to walk around the grounds. Great to be able to have dinner and breakfast at the hotel ."
United States
Ron
The price is AED 324
AED 400 total
includes taxes & fees
29 Apr - 30 Apr
Mimslyn Inn Historic Hotels Of America
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, (320 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is AED 573
AED 1,004 total
includes taxes & fees
29 Apr - 30 Apr
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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, (355 reviews)
"Wonderful getaway!"
United States
Samantha T.
The price is AED 602
AED 1,055 total
includes taxes & fees
27 Apr - 28 Apr
"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, (359 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 602
AED 1,055 total
includes taxes & fees
27 Apr - 28 Apr
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (67 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is AED 1,102
AED 1,436 total
includes taxes & fees
27 Apr - 28 Apr
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, (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 790
AED 1,570 total
includes taxes & fees
26 Apr - 27 Apr
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
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, (21 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is AED 944
AED 2,169 total
includes taxes & fees
26 Apr - 27 Apr
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Terrace/patio

The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (19 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is AED 904
AED 1,901 total
includes taxes & fees
28 Apr - 29 Apr
The Cottage on Royal - Historic Leesburg Home
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 1,480 total
includes taxes & fees
29 Apr - 30 Apr
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

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"Very nice resort with beautiful grounds and great amenities"
Debra 6-night trip
Posted 1 hour ago
Lansdowne Resort and Spa

Explore a world of travel with Expedia

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, 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 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 Old Court House Civil War Museum. A couple of additional sights to add to your agenda are Shenandoah Valley Discovery Museum and Apple Blossom Mall.
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.