The Best Historic Hotels in Winchester, VA from ￥21,137 in 2026

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

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Our top choices for Winchester historic hotels

Coffee/tea maker, fridge, microwave, oven

1. Breathtaking View with an Indoor Pool

bluemont

Anonymous traveler

￥147,313

￥303,040 total

includes taxes & fees

Sep 4 - Sep 5

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

Shepherdstown

Joseph

￥10,300

￥21,137 total

includes taxes & fees

Aug 31 - Sep 1

4 bedrooms, desk, iron/ironing board, WiFi (free)

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

Harpers Ferry

Jenn C.

￥17,691

￥62,823 total

includes taxes & fees

Aug 26 - Aug 27

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

Rileyville

Jackson C.

￥24,818

￥44,206 total

includes taxes & fees

Aug 28 - Aug 29

5. "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Rileyville

Dave A.

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

Berkeley Spring

Karen O.

￥38,148

￥68,784 total

includes taxes & fees

Aug 26 - Aug 27

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

The Plains

Jill M.

￥39,340

￥64,896 total

includes taxes & fees

Aug 26 - Aug 27

2 restaurants; breakfast, lunch, dinner, and brunch served

8. Mimslyn Inn Historic Hotels Of America

Luray

Alison Smillie

￥24,725

￥30,503 total

includes taxes & fees

Sep 17 - Sep 18

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Top Winchester Hotel Reviews

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."

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"Very clean property. Extremely helpful staff. Clean rooms. Great value."

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"

Lansdowne Resort and Spa

10/10 Excellent

"Great clean place"

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."

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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Treat yourself

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Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

1. Breathtaking View with an Indoor Pool

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

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

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

5. "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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

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

8. Mimslyn Inn Historic Hotels Of America

9. The Van Gogh Room in Villa

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

Top Winchester Hotel Reviews

Spark by Hilton Winchester

Holiday Inn Winchester Se-Historic Gateway by IHG

Courtyard by Marriott Winchester

Lansdowne Resort and Spa

Skyland

Frequently asked questions

Explore a world of travel with Expedia

Find Historic Hotels in Winchester, VA

Change your mind

Treat yourself

Be picky

Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

1. Breathtaking View with an Indoor Pool

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

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

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

5. "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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

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

8. Mimslyn Inn Historic Hotels Of America

9. The Van Gogh Room in Villa

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

Top Winchester Hotel Reviews

Spark by Hilton Winchester

Holiday Inn Winchester Se-Historic Gateway by IHG

Courtyard by Marriott Winchester

Lansdowne Resort and Spa

Skyland

Frequently asked questions

Explore a world of travel with Expedia