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.

Holiday Homes in Winchester

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Winchester holiday homes

A black leather sofa with a center console, a glass table, and two boxes on the table.

The Winchester

The Winchester
Winchester
8.8 out of 10, Excellent, (9 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 €266
includes taxes & fees
2 Aug - 3 Aug
The Winchester
Coffee/tea maker, fridge, microwave, oven

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, (11 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is €266
includes taxes & fees
2 Aug - 3 Aug
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Property grounds

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 €114
includes taxes & fees
26 Jul - 27 Jul
Cozy, Bright Home in Historic Downtown
Exterior

Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.4 out of 10, Exceptional, (12 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 €193
includes taxes & fees
23 Aug - 24 Aug
Cozy 1-bedroom in Lexington
Iron/ironing board, WiFi, bed sheets

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 €124
includes taxes & fees
25 Jul - 26 Jul
5 o'clock somewhere in Mt Sterling
Exterior

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 €119
includes taxes & fees
26 Jul - 27 Jul
1 Bedroom Bourbon House on the Hill
Living area

‘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 €151
includes taxes & fees
18 Aug - 19 Aug
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Smart TV

My Old Kentucky Home

My Old Kentucky Home
Lexington
9.8 out of 10, Exceptional, (31 reviews)
"Great place for a nice weekend visit."
United States
brian g.
The price is €216
includes taxes & fees
10 Aug - 11 Aug
My Old Kentucky Home
Interior

Charming Kentucky Stone House

Charming Kentucky Stone House
Lexington
10.0 out of 10, Exceptional, (8 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 €217
includes taxes & fees
2 Aug - 3 Aug
Charming Kentucky Stone House
Interior

The Swish & Stay I Cozy 2BR I 15m to RRG I Wi-Fi

The Swish & Stay I Cozy 2BR I 15m to RRG I Wi-Fi
Stanton
10.0 out of 10, Exceptional, (1 review)
"The room was newly renovated and really nice! The host's communication was top notch! I'll definitely stay here again the next time that I'm in the area!"
United States
Clint H.
The price is €154
includes taxes & fees
26 Jul - 27 Jul
The Swish & Stay I Cozy 2BR I 15m to RRG I Wi-Fi
Coffee/tea maker, fridge, microwave, oven

Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-

Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-
South Broadway Park
9.6 out of 10, Exceptional, (17 reviews)
"Randy was wonderful to work with! We had a lovely stay! Thank you so much!"
United States
Sharon W.
The price is €240
includes taxes & fees
27 Jul - 28 Jul
Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-
Dining

Cozy 3 bedroom home perfect for families or work.

Cozy 3 bedroom home perfect for families or work.
Lexington
9.4 out of 10, Exceptional, (3 reviews)
"Super Clean and comfortable place"
United States
Bill P.
The price is €191
includes taxes & fees
27 Jul - 28 Jul
Cozy 3 bedroom home perfect for families or work.
Property grounds

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Georgetown
8.6 out of 10, Excellent, (34 reviews)
"We enjoyed our stay here very much. Thank you!"
United States
julianne k.
The price is €159
includes taxes & fees
23 Aug - 24 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Smart TV, fireplace, offices

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, (19 reviews)
"Great location and great property!"
United States
Javon R.
The price is €237
includes taxes & fees
22 Aug - 23 Aug
Stay in a newly renovated home in the heart of Dtown Lexington
Exterior

Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is €128
includes taxes & fees
25 Jul - 26 Jul
Hunting Lodge in the City
Outdoor dining

Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Prime location

Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Prime location
Lexington
10.0 out of 10, Exceptional, (9 reviews)
"Great place to stay! "
United States
Michael T.
The price is €282
includes taxes & fees
27 Jul - 28 Jul
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Prime location
Coffee/tea maker, fridge, microwave, oven

Location, Location, Location

Location, Location, Location
Northside District
9.2 out of 10, Wonderful, (77 reviews)
"Great house! Great stay!"
United States
Michael
Location, Location, Location
Coffee/tea maker, fridge, microwave, oven

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, (14 reviews)
"This was their perfect stay for my fiancés 40th bday get away! We hope to comeback in the summer and bring our kids "
United States
Amber P.
Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
Interior

Luxurious 1-bedroom with Free Parking

Luxurious 1-bedroom with Free Parking
Lexington
9.8 out of 10, Exceptional, (70 reviews)
"The rooms were very clean and had all updated appliances. A very nice stay!"
United States
Tina B.
The price is €204
includes taxes & fees
8 Aug - 9 Aug
Luxurious 1-bedroom with Free Parking
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.

Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.
Georgetown
10.0 out of 10, Exceptional, (8 reviews)
"Mitzi is a great host, and her place is clean and cozy. We would definitely stay here again. "
United States
Shelley M.
The price is €180
includes taxes & fees
22 Aug - 23 Aug
Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.
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

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent
"The room was very clean. The lady at the front desk was very friendly and helpful. I enjoyed the hot tub, many hotels in our have hot tubs anymore."
Shannon 1-night trip
Posted 5 hours ago
Country Inn & Suites by Radisson, Georgetown, KY

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
328
Accommodation
426 Holiday Homes
Lowest Price
€114
Highest Price
€282