A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

Our top choices for Winchester historic hotels

Exterior
Coffee/tea maker, fridge, microwave, oven
Indoor pool, a heated pool
Interior

1. Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool
bluemont
United States
Anonymous traveler
AED 3,401
AED 7,059 total
includes taxes & fees
4 Sep - 5 Sep
Breathtaking View with an Indoor Pool
Exterior
Property grounds
Property grounds
WiFi (free), bed sheets

2. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
United States
Joseph
AED 238
AED 488 total
includes taxes & fees
31 Aug - 1 Sep
❤️ Secluded 1940s Romantic Tiny House on the River
Smart TV, fireplace, DVD player, books
4 bedrooms, desk, iron/ironing board, WiFi (free)
Coffee/tea maker, fridge, microwave, oven
Smart TV, fireplace, DVD player, books

3. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
United States
Jenn C.
AED 438
AED 1,488 total
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds
Coffee/tea maker, fridge, microwave, oven
Smart TV, fireplace, books, stereo
Smart TV, fireplace, books, stereo

4. "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
United States
Jackson C.
AED 573
AED 1,021 total
includes taxes & fees
24 Aug - 25 Aug
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Pool
Indoor spa tub
Exterior
Smart TV, fireplace, stereo

5. "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
United States
Dave A.
AED 573
AED 1,021 total
includes taxes & fees
24 Aug - 25 Aug
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Property grounds
Coffee/tea maker, fridge, microwave, oven
Smart TV, fireplace
Property grounds

6. Luxury And Beautiful House With Amazing Mountain View. Perfect For Getaway

Luxury And Beautiful House With Amazing Mountain View. Perfect For Getaway
Berkeley Spring
United States
Maxine
AED 882
AED 1,589 total
includes taxes & fees
24 Aug - 25 Aug
Luxury And Beautiful House With Amazing Mountain View. Perfect For Getaway
Exterior
Terrace/patio
Property grounds
Interior

7. Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
United States
Jill M.
AED 909
AED 1,492 total
includes taxes & fees
24 Aug - 25 Aug
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Exterior
2 restaurants; breakfast, lunch, dinner, and brunch served
Reception hall
2 bars/lounges

8. Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
Luray
United Kingdom
Alison Smillie
AED 571
AED 704 total
includes taxes & fees
27 Aug - 28 Aug
Mimslyn Inn Historic Hotels Of America
Outdoor dining
Pool
Property grounds
Dining

9. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
United States
Tom W.
AED 1,194
AED 1,512 total
includes taxes & fees
24 Aug - 25 Aug
The Van Gogh Room in Villa
Dining
Property grounds
Exterior
TV, fireplace, books

10. 1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .

1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
Washington
United States
Daniel R.
AED 569
AED 1,013 total
includes taxes & fees
31 Aug - 1 Sep
1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
View all properties

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Good location"
Jodi 1-night trip
Posted 13 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"Total renovation since our last stay. Very nice. Bathroom fan would be helpful. Very nice though."
Laura 1-night trip
Posted 20 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"A really luxe resort. Outside pool area super good fun and great for kids and adults alike with separate areas. Well staffed in all areas of the hotel"
Louise 1-night trip
Posted 5 days ago
Salamander Resort And Spa

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, Delightful and Serene Hundred Year Old Sweet Space Among the Gardens 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. If you're interested in local history, another option for your trip is Peaceful Secret Gardens Tiny Home - A space to relax and get away from it all..
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 75 hotel accommodations bookable on Expedia, including 3 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 Stonewall Jackson's Headquarters, Patsy Cline Historic House, and Abram's Delight. Cultural venues include Museum of the Shenandoah Valley, Bright Box Theater, and Winchester Little Theater. 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.

Explore a world of travel with Expedia