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.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winchester holiday homes

A two-story house with a porch and a front yard.

1. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
Charming Victorian Apartment | Downtown Winchester
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

2. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.6 out of 10, Exceptional, (14 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is £206
includes taxes & fees
1 Nov - 2 Nov
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A black leather sofa with a center console, a glass table, and two boxes on the table.

3. The Winchester

The Winchester
Winchester
8.6 out of 10, Excellent, (11 reviews)
"The house was clean and had all amenities needed. Love the location and was adorable. Wish I could have stayed longer. Love that there is a park across the street and the neighbors were very friendly"
United States
Gina
The price is £223
includes taxes & fees
9 Nov - 10 Nov
The Winchester
A two-story wooden cabin with a balcony, surrounded by trees.

4. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.8 out of 10, Good, (6 reviews)
"Good communication, great location and peaceful! Back deck to River does need a little work but it was overall a good stay! "
United States
Polly H.
The price is £253
includes taxes & fees
3 Nov - 4 Nov
River Relaxation - Calm Riverfront Home in Winchester Kentucky
A living room with a sofa, a television, a cabinet, and a plant.

5. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is £96
includes taxes & fees
1 Nov - 2 Nov
Cozy, Bright Home in Historic Downtown
A building with a staircase leading to a door marked with the number 218.

6. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (2 reviews)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is £93
includes taxes & fees
2 Nov - 3 Nov
1 Bedroom Bourbon House on the Hill
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

7. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.0 out of 10, Wonderful, (4 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is £97
includes taxes & fees
1 Nov - 2 Nov
5 o'clock somewhere in Mt Sterling
A stone pavilion named Hamburg Pavilion with a flagpole, surrounded by landscaped gardens and trees.

8. Midnight Lexington Newly Remodeled Designer Stay

Midnight Lexington Newly Remodeled Designer Stay
Lexington
9.8 out of 10, Exceptional, (43 reviews)
"Everything was great, the house was clean and well appointed. We had everything we needed. It was super comfortable and had a cool interior design. The location was quiet and convenient. We felt like we were close to everything from shopping to downtown. We look forward to our next stay."
United States
Michael M.
The price is £323
includes taxes & fees
3 Nov - 4 Nov
Midnight Lexington Newly Remodeled Designer Stay
Exterior

9. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is £101
includes taxes & fees
1 Nov - 2 Nov
Hunting Lodge in the City
A hot tub with two people and a bar area with bottles and a lantern.

10. Relaxing Hot Tub | S’mores Fire Pit | Garage

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (55 reviews)
"Great stay will think of this place if we ever go back to lexington"
United States
Stephanie S.
The price is £224
includes taxes & fees
8 Nov - 9 Nov
Relaxing Hot Tub | S’mores Fire Pit | Garage
A living room with a dark-colored sofa, a wooden coffee table, and a fireplace with a TV above it.

11. ‘Clara’ Just Off I-75! 2 Full Bedrooms!

‘Clara’ Just Off I-75! 2 Full Bedrooms!
Lexington
8.0 out of 10, Very good, (29 reviews)
"Great location"
United States
George L.
‘Clara’ Just Off I-75! 2 Full Bedrooms!
A two-story house with a covered patio area, string lights, and outdoor furniture.

12. Spacious King Suite w/ Game Room, Fire Pit & Patio

Spacious King Suite w/ Game Room, Fire Pit & Patio
Lexington
9.6 out of 10, Exceptional, (29 reviews)
"Excellent location and wonderful host. The home is inviting and welcoming, perfect for a family. We had a great experience "
United States
Cassidy D.
The price is £250
includes taxes & fees
9 Nov - 10 Nov
Spacious King Suite w/ Game Room, Fire Pit & Patio
A backyard patio with a grill, chairs, and a table, surrounded by a wooden fence and string lights.

13. Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location

Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location
Lexington
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay! "
United States
Michael T.
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location
A single-story house with a front porch, a small garden, and a clear pathway leading to the entrance.

14. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (20 reviews)
"We loved staying at this super lovely little house! It was perfect for two people, everything we needed and great location! If we ever plan a trip to Lexington- this is absolutely where we will stay!"
Canada
Renae
The price is £198
includes taxes & fees
2 Nov - 3 Nov
Cozy 1-bedroom in Lexington
A stone exterior with a white door, a welcome mat, and two wall-mounted lanterns.

15. Charming Kentucky Stone House

Charming Kentucky Stone House
Lexington
10.0 out of 10, Exceptional, (12 reviews)
"My wife and daughter stayed and said it was nice, clean, and easy to navigate, too. They would stay again!"
United States
Justin M.
Charming Kentucky Stone House
A modern living room with a wooden coffee table, a grey sofa, and a dining area in the background.

16. Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly

Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly
Lexington
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay! Will definitely try to stay here again when in the area."
United States
Bill B.
The price is £245
includes taxes & fees
1 Dec - 2 Dec
Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly
A modern kitchen with dark cabinetry, a stainless steel refrigerator, and a granite countertop.

17. Entire Home in Hamburg!

Entire Home in Hamburg!
Liberty Area
10.0 out of 10, Exceptional, (37 reviews)
"Very nice place. "
United States
Monte R.
The price is £325
includes taxes & fees
1 Dec - 2 Dec
Entire Home in Hamburg!
A modern kitchen with a central island, a dining area with bar stools, and a view of the outdoors through large windows.

18. Liberty Hideaway is a home designed for comfort, connection, and easy living.

Liberty Hideaway is a home designed for comfort, connection, and easy living.
Liberty Area
10.0 out of 10, Exceptional, (5 reviews)
"Great house and yard!"
United States
Staci R.
The price is £275
includes taxes & fees
2 Nov - 3 Nov
Liberty Hideaway is a home designed for comfort, connection, and easy living.
A modern kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a visible stove.

19. Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball

Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
Powell County
9.6 out of 10, Exceptional, (17 reviews)
"Great location, tons of things to do, and just about 20-25 min from the gorge."
United States
Veeresh R.
Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
A modern living room with a sofa, a TV, and a lamp. There is a kitchen visible in the background.

20. Stay in a newly renovated home in the heart of Dtown Lexington

Stay in a newly renovated home in the heart of Dtown Lexington
Lexington
9.6 out of 10, Exceptional, (23 reviews)
"Very nice place.. easy to access and get around town.."
United States
Jennifer P.
The price is £150
includes taxes & fees
1 Nov - 2 Nov
Stay in a newly renovated home in the heart of Dtown Lexington
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 Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Great location and friendly staff"
Stacy 1-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Lexington North

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
265
Accommodation
460 Holiday Homes
Lowest Price
£93
Highest Price
£325