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Our top choices for Winchester vacation homes

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

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 groupsWinchester
9.6 out of 10, Exceptional, (14 reviews)
The price is ¥21,271
¥43,944 total
includes taxes & fees
Nov 4 - Nov 5

3. The Winchester
The WinchesterWinchester
8.6 out of 10, Excellent, (11 reviews)
The price is ¥21,271
¥43,944 total
includes taxes & fees
Nov 4 - Nov 5

4. River Relaxation - Calm Riverfront Home in Winchester Kentucky
River Relaxation - Calm Riverfront Home in Winchester KentuckyWinchester
7.8 out of 10, Good, (6 reviews)

5. Cozy, Bright Home in Historic Downtown
Cozy, Bright Home in Historic DowntownMount Sterling
8.4 out of 10, Very good, (25 reviews)
The price is ¥11,029
¥19,454 total
includes taxes & fees
Nov 15 - Nov 16

6. 1 Bedroom Bourbon House on the Hill
1 Bedroom Bourbon House on the HillMount Sterling
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥17,332
¥21,191 total
includes taxes & fees
Nov 16 - Nov 17

7. 5 o'clock somewhere in Mt Sterling
5 o'clock somewhere in Mt SterlingMount Sterling
9.0 out of 10, Wonderful, (4 reviews)
The price is ¥16,307
¥20,063 total
includes taxes & fees
Nov 5 - Nov 6

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

9. Midnight Lexington Newly Remodeled Designer Stay
Midnight Lexington Newly Remodeled Designer StayLexington
9.8 out of 10, Exceptional, (43 reviews)
The price is ¥24,816
¥67,757 total
includes taxes & fees
Nov 15 - Nov 16

10. Relaxing Hot Tub | S’mores Fire Pit | Garage
Relaxing Hot Tub | S’mores Fire Pit | GarageLEXINGTON
9.4 out of 10, Exceptional, (55 reviews)
The price is ¥20,592
¥45,904 total
includes taxes & fees
Nov 15 - Nov 16

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)
The price is ¥8,351
¥24,690 total
includes taxes & fees
Nov 4 - Nov 5

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 locationLexington
10.0 out of 10, Exceptional, (11 reviews)
The price is ¥18,412
¥47,707 total
includes taxes & fees
Nov 4 - Nov 5

13. Entire Home in Hamburg!
Entire Home in Hamburg!Liberty Area
10.0 out of 10, Exceptional, (37 reviews)
The price is ¥27,573
¥68,214 total
includes taxes & fees
Dec 1 - Dec 2

14. Stay in a newly renovated home in the heart of Dtown Lexington
Stay in a newly renovated home in the heart of Dtown LexingtonLexington
9.6 out of 10, Exceptional, (23 reviews)
The price is ¥15,756
¥31,287 total
includes taxes & fees
Nov 4 - Nov 5

15. Spacious King Suite w/ Game Room, Fire Pit & Patio
Spacious King Suite w/ Game Room, Fire Pit & PatioLexington
9.4 out of 10, Exceptional, (30 reviews)
The price is ¥19,252
¥53,638 total
includes taxes & fees
Nov 9 - Nov 10

16. Cozy 1-bedroom in Lexington
Cozy 1-bedroom in LexingtonLexington
9.6 out of 10, Exceptional, (20 reviews)
The price is ¥16,307
¥41,241 total
includes taxes & fees
Nov 12 - Nov 13

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)
The price is ¥24,983
¥57,814 total
includes taxes & fees
Nov 16 - Nov 17

18. Charming Kentucky Stone House
Charming Kentucky Stone HouseLexington
10.0 out of 10, Exceptional, (12 reviews)
The price is ¥17,584
¥45,649 total
includes taxes & fees
Nov 4 - Nov 5

19. Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly
Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet FriendlyLexington
10.0 out of 10, Exceptional, (14 reviews)
The price is ¥24,195
¥55,151 total
includes taxes & fees
Nov 16 - Nov 17

20. “Ivory Inn” Modern Stay w/ Hot Tub - Greyline
“Ivory Inn” Modern Stay w/ Hot Tub - GreylineCastlewood
9.6 out of 10, Exceptional, (14 reviews)
The price is ¥18,053
¥47,290 total
includes taxes & fees
Nov 4 - Nov 5
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

Hyatt Regency Lexington
10/10 Excellent
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 |

































































