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Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Tonight
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Winchester historic hotels

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

1. Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool
bluemont
United States
Anonymous traveler
AED 3,401
AED 6,996 total
includes taxes & fees
4 Sep - 5 Sep
Breathtaking View with an Indoor Pool
Exterior
Property grounds
WiFi (free), bed sheets
Dining

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)
Exterior
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 409
AED 1,452 total
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds
Smart TV, fireplace, books, stereo
Exterior
Coffee/tea maker, fridge, microwave, oven

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
28 Aug - 29 Aug
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Pool
Indoor spa tub
Smart TV, fireplace, stereo
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.
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Property grounds
Exterior
Property grounds
Coffee/tea maker, fridge, microwave, oven

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
Karen O.
AED 882
AED 1,589 total
includes taxes & fees
7 Sep - 8 Sep
Luxury And Beautiful House With Amazing Mountain View. Perfect For Getaway
Exterior
Terrace/patio
Interior
Dining

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 1,500 total
includes taxes & fees
26 Aug - 27 Aug
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Exterior
2 bars/lounges
2 restaurants; breakfast, lunch, dinner, and brunch served
Lobby

8. Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
Luray
United Kingdom
Alison Smillie
AED 571
AED 705 total
includes taxes & fees
17 Sep - 18 Sep
Mimslyn Inn Historic Hotels Of America
Outdoor dining
1 bedroom, WiFi, bed sheets
Pool
Property grounds

9. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
United States
Tom W.
AED 1,194
AED 1,545 total
includes taxes & fees
26 Aug - 27 Aug
The Van Gogh Room in Villa
Dining
Exterior
TV, fireplace, books
Interior

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
1 Sep - 2 Sep
1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
View all properties

Top Winchester Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"The hotel and room were the cleanest place I have stayed at in a long time! Definitely would recommend it to anyone."
James 1-night trip
Posted 7 hours ago
Spark by Hilton Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"The size of king bed and pull out sofa. Bathroom was good size. The restaurant was plus to the property put no free breakfast"
Michelle 1-night trip
Posted 1 day ago
Courtyard by Marriott Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"Great clean place"
Charlotte 1-night trip
Posted 2 days ago
Lansdowne Resort and Spa
Skyland

Skyland

10/10 Excellent
"Everything thing we needed they had available. Food was good, room was clean and the staff was very friendly and helpful."
Thomas 3-night trip
Posted 2 days ago
Skyland

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 76 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 Patsy Cline Historic House, Stonewall Jackson's Headquarters, and Abram's Delight. Cultural venues include Winchester Little Theater, Museum of the Shenandoah Valley, and Bright Box 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.

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