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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winchester vacation homes

Coffee/tea maker, fridge, microwave, oven

1. 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
9.8 out of 10, Exceptional, (12 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is ￥23,205
￥48,322 total
includes taxes & fees
Sep 8 - Sep 9
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.

2. 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 ￥23,205
￥46,772 total
includes taxes & fees
Sep 8 - Sep 9
The Winchester
Exterior

3. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (1 review)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is ￥15,470
￥20,500 total
includes taxes & fees
Sep 8 - Sep 9
1 Bedroom Bourbon House on the Hill
Property grounds

4. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very Good, (23 reviews)
"Great stay as usual. Owners are super friendly & helpful. This was our 3rd time staying as we've made this our regular when visiting family in the area."
United States
Brittany K.
The price is ￥9,844
￥19,465 total
includes taxes & fees
Sep 8 - Sep 9
Cozy, Bright Home in Historic Downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

5. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.4 out of 10, Exceptional, (3 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is ￥16,173
￥21,276 total
includes taxes & fees
Sep 8 - Sep 9
5 o'clock somewhere in Mt Sterling
Terrace/patio

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

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (54 reviews)
"Stay was fine. Location is good."
United States
Lori M.
The price is ￥22,247
￥51,985 total
includes taxes & fees
Sep 15 - Sep 16
Relaxing Hot Tub | S’mores Fire Pit | Garage
Living area

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

‘Clara’ Just Off I-75! 2 Full Bedrooms!
Lexington
8.2 out of 10, Very Good, (23 reviews)
"Great location"
United States
George L.
The price is ￥8,126
￥24,122 total
includes taxes & fees
Sep 8 - Sep 9
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Exterior

8. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (16 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 ￥8,297
￥31,394 total
includes taxes & fees
Sep 14 - Sep 15
Cozy 1-bedroom in Lexington
Smart TV

9. My Old Kentucky Home

My Old Kentucky Home
Lexington
9.8 out of 10, Exceptional, (33 reviews)
"Great place for a nice weekend visit."
United States
brian g.
The price is ￥12,188
￥39,540 total
includes taxes & fees
Sep 8 - Sep 9
My Old Kentucky Home
Outdoor dining

10. 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, (9 reviews)
"Great place to stay! "
United States
Michael T.
The price is ￥39,153
￥76,821 total
includes taxes & fees
Oct 7 - Oct 8
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location
Interior

11. Charming Kentucky Stone House

Charming Kentucky Stone House
Lexington
10.0 out of 10, Exceptional, (10 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 ￥14,845
￥42,986 total
includes taxes & fees
Sep 21 - Sep 22
Charming Kentucky Stone House
Interior

12. 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, (12 reviews)
"Had a great stay! Will definitely try to stay here again when in the area."
United States
Bill B.
Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly
Smart TV, fireplace, offices

13. 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, (21 reviews)
"Very clean and just perfect for our stay."
United States
Tammy S.
The price is ￥15,626
￥32,299 total
includes taxes & fees
Sep 8 - Sep 9
Stay in a newly renovated home in the heart of Dtown Lexington
Coffee/tea maker, fridge, microwave, oven

14. 2 Miles to UK-Downtown Lex + Close to Restaurants + Top Location & Neighborhood

2 Miles to UK-Downtown Lex + Close to Restaurants + Top Location & Neighborhood
Lexington
10.0 out of 10, Exceptional, (6 reviews)
"Very nice remodeled, lower level home. Great location. Quiet Street just a few doors down from a large park.Close to UK campus and especially for the track and field complex. Hosts were very accommodating and helpful."
United States
Jon S.
2 Miles to UK-Downtown Lex + Close to Restaurants + Top Location & Neighborhood
Coffee/tea maker, fridge, microwave, oven

15. 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, (4 reviews)
"Great house and yard!"
United States
Staci R.
The price is ￥21,415
￥51,476 total
includes taxes & fees
Sep 9 - Sep 10
Liberty Hideaway is a home designed for comfort, connection, and easy living.
Coffee/tea maker, fridge, microwave, oven

16. 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.
Entire Home in Hamburg!
Terrace/patio

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

“Ivory Inn” Modern Stay w/ Hot Tub - Greyline
Castlewood
9.6 out of 10, Exceptional, (12 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 ￥18,173
￥49,387 total
includes taxes & fees
Sep 8 - Sep 9
“Ivory Inn” Modern Stay w/ Hot Tub - Greyline
Outdoor dining

18. 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, (28 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 ￥21,251
￥60,766 total
includes taxes & fees
Sep 14 - Sep 15
Spacious King Suite w/ Game Room, Fire Pit & Patio
Interior

19. Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
Lexington
10.0 out of 10, Exceptional, (18 reviews)
"Our stay was great! Awesome communication with the host, and it was in such a convenient location. We would stay again!"
United States
Caroline B.
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
3 bedrooms, iron/ironing board, WiFi (free), bed sheets

20. "The Kearney" BRIGHT MODERN STAY w/ Yard - 3BR

"The Kearney" BRIGHT MODERN STAY w/ Yard - 3BR
Lexington
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed our stay at The Kearney! It was clean, had very comfortable beds, and we loved roasting s'mores by the fire pit! Everything was just as advertised, and the proximity to the Kentucky Horse Park was very convenient for us. We will definitely stay again!"
United States
Sandra G.
The price is ￥15,285
￥45,674 total
includes taxes & fees
Sep 8 - Sep 9
"The Kearney" BRIGHT MODERN STAY w/ Yard - 3BR
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

Hyatt Regency Lexington

10/10 Excellent
"Stayed for Lexington Comic Con so we could travel back in forth inside which was nice. Also within steps of Lex Live. Breakfast was delicious inside property. The pool area was clean with plenty of towels and water was great temperature. Hyatt made our stay very comfortable."
Ann 1-night trip
Posted 1 hour ago
Hyatt Regency Lexington

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
327
Accommodation
446 Vacation Homes
Lowest Price
￥19,465
Highest Price
￥90,868