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Find Historic Hotels in Winchester, KY

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Check availability on Winchester Historic Hotels

Tonight
Aug 6 - Aug 7
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Aug 7 - Aug 8
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Aug 8 - Aug 10
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Aug 15 - Aug 17

Top Winchester Historic Hotels

Top Winchester Hotel Reviews

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"We love the Elwood! Fourth time staying this summer and back in two weeks. "
Wendy 3-night trip
Posted 17 hours ago
Elwood Hotel & Suites

Frequently asked questions

What should I expect on my historical trip to Winchester?
You'll probably want to seek out the places with historical relevance during your vacation in Winchester. Why not absorb the local color with a visit to the restaurants?
What's the best accommodation in Winchester that's close to historical sites?
Based on our travel expertise, Red Roof Inn Lexington - Winchester is a top property for history seekers booking on Expedia, and it features free WiFi and free parking. Fort Boonesborough State Park is a short 19-minute drive away.
How many historical hotels are located in Winchester?
Winchester is home to 21 hotels and other accommodations bookable on Expedia though you won't find many designated historic hotels.
What are the most important historical places and other sights to visit in Winchester?
Winchester is notable for landmarks like Bluegrass Heritage Museum. Natural beauty is on display at Lykins Park, College Park, and GRCHS Baseball Field. A couple of additional sights to add to your agenda are Southwind Golf Course and Winchester Opera House.
What is a historic hotel like in Winchester?
When you book a historic hotel, you'll spend a night or two in a place that has a national historic designation. A castle, a palace or even a pub or an old police station can be turned into a historic hotel as long as it has special significance. Traditional architecture and period features are often preserved in the public spaces and guestrooms of these historic hotels in Winchester, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is more common in the U.S. but overall the terms are quite similar. The architecture and actual building of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value and how it shaped the community.
Do historic hotels in Winchester have modern facilities?
Hotels have the safety features and modern conveniences you've come to expect, though efforts have been made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in a hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Winchester, you won't find a place that's uncomfortable for guests or simply rundown.