An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Find Historic Hotels in Winchester, KY from CA $268

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Check availability on Winchester Historic Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Winchester historic hotels

A log cabin interior with a wooden desk, leather armchair, and a patterned rug.
Two blue Adirondack chairs on a concrete path surrounded by leaf-covered ground and trees.
A rustic cabin surrounded by dense greenery, with a stone wall in the foreground and a wooden staircase leading up to the entrance.
A log cabin bedroom with a large bed, wooden dresser, and a window with a view of trees.

1. Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
United States
Anonymous traveller
CA $146
CA $268 total
includes taxes & fees
Oct 4 - Oct 5
Unique Stay in a 1907 Log Cabin on The Kentucky River
A gated entrance with a stone wall, a tree, and white hydrangea flowers.
A small log cabin with a red door, surrounded by a grassy field and trees.
A kitchen with a large window, a sink, and wooden cabinets.
A log cabin interior with a cozy seating area, a dining table, and a bookshelf.

2. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
United Kingdom
Siobann S.
CA $461
CA $690 total
includes taxes & fees
Oct 4 - Oct 5
Cabin in Kentucky Horse Country
A woman in a blue floral dress opening a glass door to a patio with a dog, a potted plant, and a vase of flowers.
A hallway with wooden flooring, white walls, and a staircase leading to another room.
A bright hallway with a white ceiling, a hanging light fixture, a small table with plants, and a potted plant on the floor.
A modern kitchen with a sliding barn door entrance, a dining area with a table and chairs, and a black spiral staircase.

3. East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to Downtown
Georgetown
United States
Julia A.
CA $177
CA $328 total
includes taxes & fees
Oct 5 - Oct 6
East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to Downtown
A modern kitchen with a central island, a dining area with a round table, a sofa, and artwork on the walls.
A modern kitchen with a central island, a dining area with a round table, a sofa, and a TV mounted on the wall.
A modern hotel room with a large bed, a flat-screen TV, and a city view.
A modern living room with a wooden dining table, a sofa, and artwork on the walls.

4. Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
United States
Michele G.
CA $211
CA $399 total
includes taxes & fees
Oct 4 - Oct 5
Bourbon Condo Downtown Lexington
A modern living room with a dining area, large windows, and a ceiling fan.
Exterior detail
A bedroom with a tufted headboard bed, a window with curtains, a ceiling fan, and a bedside table with a lamp.
A modern living room with a large window, a white sofa, a white console table with plants, and a flat-screen TV mounted on the wall.

5. Quiet Downtown Lexington Bougie Apartment

Quiet Downtown Lexington Bougie Apartment
Downtown Lexington
United States
Bernadette R.
CA $195
CA $345 total
includes taxes & fees
Oct 25 - Oct 26
Quiet Downtown Lexington Bougie Apartment
A log cabin with a wooden door and window, number 318 visible on the door.
A bedroom with a large bed, a bedside table with a lamp, a window with curtains, and a mirror on the wall.
A log cabin with a red door, a stone pillar, a lantern, a bench, and a potted plant.
A dining room with a wooden table, four chairs, a fireplace with a vase, and a painting above it.

6. Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Downtown Lexington
United States
Cindy S.
CA $304
CA $682 total
includes taxes & fees
Oct 4 - Oct 5
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
A two-story house with a front porch, a number 162 sign, and a small garden.
A compact kitchen with wooden cabinets, a stainless steel refrigerator, and a dining table with placemats.
A bedroom with a bed, a chair, a fireplace, and a television.
A living room with a sofa, armchairs, a coffee table, a rug, a lamp, a plant, and framed pictures on the wall.

7. Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms

Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
Downtown Lexington
United States
Anthony
CA $410
CA $704 total
includes taxes & fees
Oct 11 - Oct 12
Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
View all properties

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"It was a pleasurable experience"
Richard 4-night trip
Posted 8 hours ago
GuestHouse Lexington
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"It was a beautiful hotel & room right in town. Loved our king room so much. The staff was amazing & so friendly. The breakfast was very good. The only issue is the parking. You can park on the street where there’s no open spaces or valet park. So you have to valet park. Daily charge to park plus tipping your valet. They also don’t tell you that up front."
Barry 1-night trip
Posted 12 hours ago
Elwood Hotel & Suites
Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"Friendly staff, nice hotel, good selection of breakfast items."
Mark 2-night trip
Posted 17 hours ago
Hyatt Place Lexington
Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg

10/10 Excellent
"Very smooth check in process and overall very quiet property. Gas stations directly next to it and stores down the road."
Jeremy 2-night trip
Posted 18 hours ago
Motel 6 Lexington I-75 Hamburg
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Great place to stay. Needing a face lift but clean and convenient. Great staff."
SUSAN 1-night trip
Posted 19 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"It was great. Exceeded my expectations. They even shuttled me to a restaurant and not just to and from the airport. And the people were super nice."
Brownell 2-night trip
Posted 1 day ago
Embassy Suites by Hilton Lexington Green
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Nice breakfast. Clean and spacious room."
Ronn 1-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Lexington North
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent
"Great stay- clean and homey! Would def go back!"
Marcy 2-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Georgetown, KY
Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

10/10 Excellent
"This hotel has clean rooms, great staff, and breakfast is pretty good. Parking is good."
Brenda 2-night trip
Posted 2 days ago
Microtel Inn by Wyndham Lexington

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?
How many historical hotels are located in Winchester?
Winchester is home to 23 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 College Park, GRCHS Baseball Field, and Community Park. A couple of additional sights to add to your agenda are Cassell Creek 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.

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