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Check availability on Winchester Historic Hotels

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Winchester historic hotels

Interior

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 588 total
includes taxes & fees
8 Jul - 9 Jul
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Exterior

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,004 reviews)
"Lovely historic Inn."
United States
Karen
The price is AED 388
AED 479 total
includes taxes & fees
22 Jul - 23 Jul
Mimslyn Inn Historic Hotels Of America
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (79 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AED 272
AED 526 total
includes taxes & fees
28 Jul - 29 Jul
❤️ Secluded 1940s Romantic Tiny House on the River
Interior

Rural Home, Hot Tub, Campfire, Hardwood Floors

Rural Home, Hot Tub, Campfire, Hardwood Floors
Harpers Ferry
9.4 out of 10, Exceptional, (85 reviews)
"We enjoyed this house very comfy cozy we stayed because we had a celebration of life and me and my family were able to just unwind here thank u so much we loved it and the jacuzzi was wonderful "
United States
Jennifer B.
The price is AED 370
AED 1,401 total
includes taxes & fees
9 Jul - 10 Jul
Rural Home, Hot Tub, Campfire, Hardwood Floors
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, (365 reviews)
"Fantastic stay! Will definitely come back!"
United States
Tristan T.
The price is AED 558
AED 999 total
includes taxes & fees
9 Jul - 10 Jul
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Smart TV, fireplace, DVD player, books

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is AED 467
AED 1,517 total
includes taxes & fees
19 Jul - 20 Jul
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Outdoor spa tub

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Harpers Ferry
9.6 out of 10, Exceptional, (18 reviews)
"The house was clean and accommodating. It was truly right next door to the river riders establishment. The hot tub was AMAZING! Wish I had more time to enjoy it. We would definitely rent it again "
United States
Lynette M.
The price is AED 397
AED 1,434 total
includes taxes & fees
12 Jul - 13 Jul
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Smart TV, table tennis, books

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (23 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is AED 944
AED 2,175 total
includes taxes & fees
8 Jul - 9 Jul
Walk to Old Rag | Hot Tub | Mountain Farmhouse
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, (367 reviews)
"It was exactly what we needed, out of the way and in nature, but close to beautiful attractions and grocery stores "
United States
Aaron A.
The price is AED 529
AED 961 total
includes taxes & fees
8 Jul - 9 Jul
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Dining

Entire Colonial Private 3BR House Beside The Inn.Fast WiFi,tub,queen size bed

Entire Colonial Private 3BR House Beside The Inn.Fast WiFi,tub,queen size bed
Washington
10.0 out of 10, Exceptional, (127 reviews)
"We loved this accomodation! In a great little town and near the skyline drive. It was so peaceful and comfortable - only wish we had stayed longer!"
United Kingdom
Lily P.
The price is AED 579
AED 973 total
includes taxes & fees
20 Jul - 21 Jul
Entire Colonial Private 3BR House Beside The Inn.Fast WiFi,tub,queen size bed
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

8/10 Good
"nice place to stay would recommend for others. very nice breakfast"
Michael 1-night trip
Posted 10 hours ago
Fairfield Inn & Suites by Marriott Winchester

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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 family-friendly area.
What's the best hotel in Winchester to be near historical sites?
Based on our travel expertise, Secret Gardens Carriage House A 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. A couple of other options to soak up the local history 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 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 George Washington's Office. 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.