Historic Hotels & Resorts in Winchester from NZ$178

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Historic Hotels

Our top choices for Winchester historic hotels

Fitness facility
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"Great stay! Would definitely would stay again!"
United States
James
The price is NZ$200
includes taxes & fees
18 Jan - 19 Jan
Hampton Inn Winchester-University/Mall Area
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Historic Bluemont Village Home
Bluemont
10.0 out of 10, Exceptional, (39 reviews)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
United States
Mary S.
The price is NZ$737
includes taxes & fees
11 Jan - 12 Jan
Historic Bluemont Village Home
Exterior
Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool
bluemont
9.8 out of 10, Exceptional, (263 reviews)
"We had such a wonderful time at this gorgeous house! It was clean, comfortable, spacious and very relaxing. Our group had kids and adults of all ages and everyone had a fantastic time. The brewery next door is an added bonus, and we didn’t have any issues with noise or crowds. We will definitely stay here again."
United States
Laura D.
The price is NZ$2,968
includes taxes & fees
15 Jan - 16 Jan
Breathtaking View with an Indoor Pool
Exterior
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,007 reviews)
"Very nice stay! Beth at the front desk was warm and welcoming!"
United States
Tyler
The price is NZ$178
includes taxes & fees
19 Jan - 20 Jan
Mimslyn Inn Historic Hotels Of America
Meeting facility
Airlie Hotel

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (336 reviews)
"Gorgeous grounds. Worth the visit. "
United States
mary lynne
The price is NZ$323
includes taxes & fees
15 Jan - 16 Jan
Airlie Hotel
Smart TV, ping pong, books
Walk to Old Rag* hot tub* 360 mountain views

Walk to Old Rag* hot tub* 360 mountain views

Walk to Old Rag* hot tub* 360 mountain views
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$1,018
includes taxes & fees
11 Jan - 12 Jan
Walk to Old Rag* hot tub* 360 mountain views
Exterior
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (68 reviews)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is NZ$182
includes taxes & fees
19 Jan - 20 Jan
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds
Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (11 reviews)
"Great location in Lower Harper's Ferry. We completely enjoyed our stay. Will definitely be staying again in the future."
United States
Andrew R.
The price is NZ$386
includes taxes & fees
11 Jan - 12 Jan
Best location! Baltimore Suite @ historic 1799 Inn
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.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville
10.0 out of 10, Exceptional, (342 reviews)
"Everything was perfect for our stay. "
United States
Debbie O.
The price is NZ$455
includes taxes & fees
13 Jan - 14 Jan
"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

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville
10.0 out of 10, Exceptional, (352 reviews)
"Great place!"
United States
Donald C.
The price is NZ$455
includes taxes & fees
13 Jan - 14 Jan
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
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.
View all properties

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
" Very comfortable bed."
GARY 1-night trip
Posted 4 days ago
La Quinta Inn & Suites 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, Secret Gardens Carriage House 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 Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed 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 76 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 The Kernstown Battlefield. Cultural venues include Bright Box Theater, Museum of the Shenandoah Valley and Winchester Little Theater. 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.