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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Our top choices for Winchester vacation homes

1. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
The price is ¥11,502
¥63,478 total
includes taxes & fees
Nov 4 - Nov 5
Charming Victorian Apartment | Downtown Winchester

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 ¥21,271
¥43,944 total
includes taxes & fees
Nov 4 - Nov 5
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

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 ¥21,271
¥43,944 total
includes taxes & fees
Nov 4 - Nov 5
The Winchester

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.
River Relaxation - Calm Riverfront Home in Winchester Kentucky

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 ¥11,029
¥19,454 total
includes taxes & fees
Nov 15 - Nov 16
Cozy, Bright Home in Historic Downtown

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 ¥17,332
¥21,191 total
includes taxes & fees
Nov 16 - Nov 17
1 Bedroom Bourbon House on the Hill

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 ¥16,307
¥20,063 total
includes taxes & fees
Nov 5 - Nov 6
5 o'clock somewhere in Mt Sterling

8. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is ¥17,016
¥20,843 total
includes taxes & fees
Nov 4 - Nov 5
Hunting Lodge in the City

9. 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 ¥24,816
¥67,757 total
includes taxes & fees
Nov 15 - Nov 16
Midnight Lexington Newly Remodeled Designer Stay

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 ¥20,592
¥45,904 total
includes taxes & fees
Nov 15 - Nov 16
Relaxing Hot Tub | S’mores Fire Pit | Garage

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.
The price is ¥8,351
¥24,690 total
includes taxes & fees
Nov 4 - Nov 5
‘Clara’ Just Off I-75! 2 Full Bedrooms!

12. 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.
The price is ¥18,412
¥47,707 total
includes taxes & fees
Nov 4 - Nov 5
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location

13. Entire Home in Hamburg!

Entire Home in Hamburg!
Liberty Area
10.0 out of 10, Exceptional, (37 reviews)
"We loved our stay! Beautiful home. Very clean and so well stocked"
United States
Parice M.
The price is ¥27,573
¥68,214 total
includes taxes & fees
Dec 1 - Dec 2
Entire Home in Hamburg!

14. 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 ¥15,756
¥31,287 total
includes taxes & fees
Nov 4 - Nov 5
Stay in a newly renovated home in the heart of Dtown Lexington

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

Spacious King Suite w/ Game Room, Fire Pit & Patio
Lexington
9.4 out of 10, Exceptional, (30 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 ¥19,252
¥53,638 total
includes taxes & fees
Nov 9 - Nov 10
Spacious King Suite w/ Game Room, Fire Pit & Patio

16. 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 ¥16,307
¥41,241 total
includes taxes & fees
Nov 12 - Nov 13
Cozy 1-bedroom in Lexington

17. 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 ¥24,983
¥57,814 total
includes taxes & fees
Nov 16 - Nov 17
Liberty Hideaway is a home designed for comfort, connection, and easy living.

18. 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.
The price is ¥17,584
¥45,649 total
includes taxes & fees
Nov 4 - Nov 5
Charming Kentucky Stone House

19. 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 ¥24,195
¥55,151 total
includes taxes & fees
Nov 16 - Nov 17
Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly

20. “Ivory Inn” Modern Stay w/ Hot Tub - Greyline

“Ivory Inn” Modern Stay w/ Hot Tub - Greyline
Castlewood
9.6 out of 10, Exceptional, (14 reviews)
"Really really nice house and the hosts were fabulous-I spoke with Allen and let me just say- top notch service all around!! The location was great and the house was perfect for our family get away. "
United States
Susan H.
The price is ¥18,053
¥47,290 total
includes taxes & fees
Nov 4 - Nov 5
“Ivory Inn” Modern Stay w/ Hot Tub - Greyline
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

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
263
Accommodation
454 Vacation Homes
Lowest Price
¥19,454
Highest Price
¥68,214