Winchester Hotel Guide - Historic Hotels in Winchester, Virginia

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Our top choices for Winchester historic hotels

1. ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Winchester
The price is €137
includes taxes & fees
7 Nov - 8 Nov
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is €90
includes taxes & fees
15 Nov - 16 Nov
❤️ Secluded 1940s Romantic Tiny House on the River

3. Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,012 reviews)
"Lovely Inn to stay at--- pleasant folks Good restaurant and a very nice spa Love the ambiance of this old building."
United States
Anne
The price is €130
includes taxes & fees
1 Dec - 2 Dec
Mimslyn Inn Historic Hotels Of America

4. "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, (378 reviews)
"Amazing location and perfect get away for two"
United States
Heather R.
The price is €247
includes taxes & fees
9 Nov - 10 Nov
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

5. Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (369 reviews)
"Great and peaceful stay"
United States
Raquel
The price is €159
includes taxes & fees
23 Nov - 24 Nov
Airlie Hotel

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
9.0 out of 10, Wonderful, (7 reviews)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
United States
Jill M.
The price is €347
includes taxes & fees
12 Nov - 13 Nov
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

7. The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi

The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
Washington
10.0 out of 10, Exceptional, (132 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is €246
includes taxes & fees
16 Nov - 17 Nov
The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi

8. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (74 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveller
The price is €388
includes taxes & fees
7 Nov - 8 Nov
The Van Gogh Room in Villa

9. Downtown Cottage with Fire Pit

Downtown Cottage with Fire Pit
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (23 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is €490
includes taxes & fees
9 Nov - 10 Nov
Downtown Cottage with Fire Pit

10. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (40 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is €462
includes taxes & fees
8 Nov - 9 Nov
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
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.

Frequently Asked Questions

What should a history buff expect from a stay in Winchester?

Visitors love the significant historical sites they discover on a trip to Winchester. The major shopping area and top-notch restaurants are some of the places to visit while you're here. You can also discover the theatre scene during your holiday to this vibrant area.

What's the best accommodation in Winchester to absorb the local history?

Based on our travel expertise, Delightful and Serene Hundred Year Old Sweet Space Among the Gardens is a top guest house on Expedia for those interested in history, and it features on-site 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 stay is Peaceful Secret Gardens Tiny Home - A space to relax and get away from it all..

How many historically relevant hotels are located in Winchester?

Winchester has 75 hotels 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 George Washington's Office. 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 itinerary are Shenandoah Valley Discovery Museum and Apple Blossom Mall.

What is a historic hotel like in Winchester?

By choosing a historic hotel, you can sleep in a place that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be considered a historic hotel provided that it's of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Winchester, giving a historical feel.

What is the difference between a historic hotel and a heritage hotel?

These terms are similar. "Historic hotel" is more commonly used in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to emphasise the architecture and building. Mainly a heritage hotel draws meaning from the place's cultural value and how it influenced the community.

Do historic hotels in Winchester have modern facilities?

Yes, every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Visitors should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's uncomfortable for guests or rundown.