Find Historic Hotels in Winchester, VA

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Check availability on Winchester Historic Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Winchester Historic Hotels

Hampton Inn Winchester-University/Mall Area
Porch

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! "
The price is AED 391
AED 443 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Winchester-University/Mall Area
Airlie Hotel
Fireplace

Airlie Hotel

3.5 star property
8.8 out of 10, Excellent, (319)
"We love the old charm this hotel offers, while the rooms are cozy and new!"
The price is AED 493
AED 595 total
includes taxes & fees
8 Oct - 9 Oct
Airlie Hotel
Mimslyn Inn Historic Hotels Of America
Exterior

Mimslyn Inn Historic Hotels Of America

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Wonderful property, would stay there again "
The price is AED 466
AED 575 total
includes taxes & fees
27 Oct - 28 Oct
Mimslyn Inn Historic Hotels Of America
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is AED 149
AED 388 total
includes taxes & fees
19 Oct - 20 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Pool

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

10.0 out of 10, Exceptional, (331)
"Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. "
The price is AED 523
AED 921 total
includes taxes & fees
8 Oct - 9 Oct
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
The Creekside Cottage: Downtown | Pet-Friendly
Property grounds

The Creekside Cottage: Downtown | Pet-Friendly

10.0 out of 10, Exceptional, (2)
"pet friendly, perfect spot in relation to downtown,,,,very quaint loved it!!!!"
The price is AED 808
AED 1,335 total
includes taxes & fees
7 Oct - 8 Oct
The Creekside Cottage: Downtown | Pet-Friendly
Downtown: Explore Shepherdstown from cozy 1br apartment
TV

Downtown: Explore Shepherdstown from cozy 1br apartment

9.4 out of 10, Exceptional, (16)
"We were lucky to find this perfectly located place! Very clean, well-stocked with coffee in the nice kitchen, good bed. If it had reading lamps by the bed and the sofa, and more hooks/rods in the bathroom for towels, it would have been perfection. I would stay there again."
The price is AED 441
AED 751 total
includes taxes & fees
7 Oct - 8 Oct
Downtown: Explore Shepherdstown from cozy 1br apartment
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor spa tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10.0 out of 10, Exceptional, (339)
"We had a great time and can't wait to return"
The price is AED 579
AED 1,002 total
includes taxes & fees
9 Oct - 10 Oct
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
The Cottage on Royal - Historic Leesburg Home
Terrace/patio

The Cottage on Royal - Historic Leesburg Home

10.0 out of 10, Exceptional, (15)
"Within walking distance to everything important."
The price is AED 804
AED 1,732 total
includes taxes & fees
28 Oct - 29 Oct
The Cottage on Royal - Historic Leesburg Home
Secluded,Mountain View, House, Hot tub, Wifi, King beds, Near Cacapon State Park
Exterior

Secluded,Mountain View, House, Hot tub, Wifi, King beds, Near Cacapon State Park

10.0 out of 10, Exceptional, (268)
"It was a very nice place very cozy and comfortable."
The price is AED 735
AED 2,355 total
includes taxes & fees
21 Oct - 22 Oct
Secluded,Mountain View, House, Hot tub, Wifi, King beds, Near Cacapon State Park
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.
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Top Winchester Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Coffee pots need to be cleaned daily - refeerring to the bas"
SUSAN 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA

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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, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed 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. A couple of other options to soak up the local history include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 79 hotel accommodations bookable on Expedia, including 4 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 Bright Box Theater, Winchester Little Theater, and Museum of the Shenandoah Valley. 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.