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.

Winchester Vacation Rentals

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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

A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

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 CA $205
CA $428 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $205
CA $428 total
includes taxes & fees
Sep 7 - Sep 8
The Winchester
A building with a staircase leading to a door marked with the number 218.

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 CA $137
CA $181 total
includes taxes & fees
Sep 7 - Sep 8
1 Bedroom Bourbon House on the Hill
A Farmers' Market pavilion with a green signboard, white structural elements, and a covered area with yellow bollards.

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 CA $87
CA $172 total
includes taxes & fees
Sep 7 - Sep 8
Cozy, Bright Home in Historic Downtown
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

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 CA $143
CA $188 total
includes taxes & fees
Sep 8 - Sep 9
5 o'clock somewhere in Mt Sterling
A hot tub with two people and a bar area with bottles and a lantern.

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 CA $132
CA $380 total
includes taxes & fees
Sep 7 - Sep 8
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.

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 CA $72
CA $213 total
includes taxes & fees
Sep 7 - Sep 8
‘Clara’ Just Off I-75! 2 Full Bedrooms!
A single-story house with a front porch, a small garden, and a clear pathway leading to the entrance.

8. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (15 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 CA $73
CA $279 total
includes taxes & fees
Sep 14 - Sep 15
Cozy 1-bedroom in Lexington
A living room with a fireplace, a staircase, and a TV mounted above it.

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 CA $108
CA $351 total
includes taxes & fees
Sep 14 - Sep 15
My Old Kentucky Home
A backyard patio with a grill, chairs, and a table, surrounded by a wooden fence and string lights.

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 CA $153
CA $432 total
includes taxes & fees
Sep 7 - Sep 8
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location
A stone exterior with a white door, a welcome mat, and two wall-mounted lanterns.

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 CA $106
CA $349 total
includes taxes & fees
Sep 9 - Sep 10
Charming Kentucky Stone House
A modern living room with a wooden coffee table, a grey sofa, and a dining area in the background.

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.
The price is CA $172
CA $457 total
includes taxes & fees
Sep 7 - Sep 8
Stylish Hartland Location. 2 Kings, 2 Full Baths, Fenced Yard, Pet Friendly
A modern living room with a sofa, a TV, and a lamp. There is a kitchen visible in the background.

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 CA $138
CA $288 total
includes taxes & fees
Sep 7 - Sep 8
Stay in a newly renovated home in the heart of Dtown Lexington
A modern kitchen with grey cabinets, stainless steel appliances, and a white tiled backsplash.

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.
The price is CA $176
CA $398 total
includes taxes & fees
Sep 7 - Sep 8
2 Miles to UK-Downtown Lex + Close to Restaurants + Top Location & Neighborhood
A modern kitchen with a central island, a dining area with bar stools, and a view of the outdoors through large windows.

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 CA $192
CA $465 total
includes taxes & fees
Sep 9 - Sep 10
Liberty Hideaway is a home designed for comfort, connection, and easy living.
A modern kitchen with dark cabinetry, a stainless steel refrigerator, and a granite countertop.

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.
The price is CA $381
CA $826 total
includes taxes & fees
Oct 5 - Oct 6
Entire Home in Hamburg!
A covered outdoor deck with wooden furniture, a hot tub, and a view of the surrounding area.

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 CA $178
CA $466 total
includes taxes & fees
Sep 8 - Sep 9
“Ivory Inn” Modern Stay w/ Hot Tub - Greyline
A two-story house with a covered patio area, string lights, and outdoor furniture.

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 CA $113
CA $445 total
includes taxes & fees
Sep 8 - Sep 9
Spacious King Suite w/ Game Room, Fire Pit & Patio
A kitchen with a modern design, featuring a stainless steel sink, a window with a view of the outside, and a colorful tiled backsplash.

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.
The price is CA $154
CA $430 total
includes taxes & fees
Sep 7 - Sep 8
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
A bedroom with a large bed, a ceiling fan, a painting on the wall, and a window.

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 CA $135
CA $408 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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Melissa and Louis at the front desk are exceptional employees. They welcomed me in the most personal way and helped me with directions and everything I needed. My room was conveniently close to the front desk and the breakfast was fuller (with more items and options) than other comparable hotels I have stayed in. My room did not have a luggage rack but Melissa quickly found one for me. The WiFi was a bit slow, but I still was able to do my work. The only problem I encountered during the stay was lack of parking close to the front desk and obstructions due to the concrete work going on blocking the front entrance entirely on my departure day and also blocking the side entrance with workers standing around, making backing out of my parking place challenging. I was glad my key worked to get in the side door, but I don't know what I would have done if I had found the entrance completely blocked off if the day prior when I was checking in. But overall, the location was perfect as was the room and breakfast and the help at the front desk was EXTRAORDINARY. Those two employees deserve kudos for service."
Nancy 1-night trip
Posted 11 hours ago
Fairfield Inn & Suites by Marriott Lexington North

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
326
Accommodation
446 Vacation Homes
Lowest Price
CA $172
Highest Price
CA $826

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