Find Historic Hotels in Winchester, VA

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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 AED 221
AED 555 total
includes taxes & fees
5 Nov - 6 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 AED 152
AED 361 total
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, (1,008 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 AED 434
AED 535 total
includes taxes & fees
1 Dec - 2 Dec
Mimslyn Inn Historic Hotels Of America

4. "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, (390 reviews)
"What a great place they have here."
United States
James W.
The price is AED 578
AED 1,022 total
includes taxes & fees
11 Nov - 12 Nov
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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 AED 526
AED 656 total
includes taxes & fees
23 Nov - 24 Nov
Airlie Hotel

6. "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 AED 602
AED 1,004 total
includes taxes & fees
9 Nov - 10 Nov
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

7. "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, (345 reviews)
"Balcony, hot tub, and cabin were all very private with great Mountain Views which was exactly what I was looking for"
United States
Elise D.
The price is AED 624
AED 1,084 total
includes taxes & fees
16 Nov - 17 Nov
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

8. 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 AED 909
AED 1,413 total
includes taxes & fees
12 Nov - 13 Nov
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

9. 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 traveler
The price is AED 1,286
AED 1,520 total
includes taxes & fees
5 Nov - 6 Nov
The Van Gogh Room in Villa

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 AED 1,469
AED 1,842 total
includes taxes & fees
5 Nov - 6 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 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 vibrant 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 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 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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