Historic Hotels & Resorts in Winchester from NZ$182

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Check availability on Winchester Historic Hotels

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

Our top choices for Winchester historic hotels

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (72 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is NZ$248
includes taxes & fees
20 Apr - 21 Apr
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice hotel with lots of history "
United States
Patrick
The price is NZ$182
includes taxes & fees
12 Apr - 13 Apr
Mimslyn Inn Historic Hotels Of America
Property grounds

"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, (319 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is NZ$513
includes taxes & fees
13 Apr - 14 Apr
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Pool

"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, (351 reviews)
"Everything was perfect for our stay. "
United States
Debbie O.
The price is NZ$523
includes taxes & fees
13 Apr - 14 Apr
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Outdoor spa tub

"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, (359 reviews)
"Great place!"
United States
Donald C.
The price is NZ$638
includes taxes & fees
26 Apr - 27 Apr
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (67 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is NZ$669
includes taxes & fees
6 Apr - 7 Apr
The Van Gogh Room in Villa
Outdoor dining

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, (37 reviews)
"My husband and I had a memorable stay at Villa Maud over New Year. Maud was a gracious host and we very much enjoyed the comforts of our honeymoon villa. Maud is a talented artist and her impressive work adorns the villa. One of the highlights was meeting Tim the donkey"
United States
jo H.
The price is NZ$835
includes taxes & fees
6 Apr - 7 Apr
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Property grounds

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
9.8 out of 10, Exceptional, (89 reviews)
"Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is."
United States
Lisa S.
The price is NZ$766
includes taxes & fees
6 Apr - 7 Apr
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Smart TV, ping pong, books

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (21 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is NZ$1,044
includes taxes & fees
6 Apr - 7 Apr
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Meeting facility

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (342 reviews)
"The grounds are beautiful. We stayed right after the holidays so not as many amenities were available as are during other times of the year. The room was clean and comfortable, and the staff was helpful."
United States
Jennifer
The price is NZ$410
includes taxes & fees
6 Apr - 7 Apr
Airlie Hotel
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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"There was a busy area for breakfast but many choices nearby."
Marilyn 1-night trip
Posted 4 hours ago
Travelodge by Wyndham Winchester

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 family-friendly area.
What's the best accommodation in Winchester to absorb the local history?
Based on our travel expertise, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed 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. A couple of other options near historic sites include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
How many historically relevant hotels are located in Winchester?
Winchester has 77 hotels 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 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 Jim Barnett Park.
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.