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Holiday villas in Winchester, KY

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All 18 Rentals in the Winchester Area
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The following rentals are within 25 kilometers of Winchester, Kentucky.

From
€103
Per Night
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1 / 8
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Lexington
1 Bedroom, 1 Bathroom, Sleeps 4
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From
€123
Per Night
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1 / 13
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Lexington
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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From
€381
Per Night
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1 / 10
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Lexington
3 Bedrooms, 3 Bathrooms, Sleeps 10
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From
€410
Per Night
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1 / 17
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Lexington
4 Bedrooms, 4 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Back in 1894, a man named John McCann decided to move his family to the metropolitan area of Fayette County. He purchased a one acre lot on West Third Street and spent three years $ 18,000 into building a 5,800 sq foot Colonial Revival Mansion with every modern convenience. Gracious curved glass... View all property information
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5 of 5 stars Reviewed 19 May 2014
We were in town for a bachelor weekend enjoying the Kentucky Bourbon Trail. The house was amazing and there was plenty of room for the seven of us. Many excellent restaurants...
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From
€80
Per Night
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1 / 4
Pine Ridge
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Sitting in the heart of the Daniel Boone National Forest and surrounded by a scenic wonderland, our Log Cabin is conveniently located at the entrance to the Red River Gorge and Rock Bridge, a natural sandstone arch that extends across Swift Creek. The Log Cabin is a real, hand-hewn log cabin with... View all property information
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5 of 5 stars Reviewed 20 October 2014
My Husband & I spent our Honey moon at Red River Gorge & we rented the Telstar Cabin & we were just so happy & blown away with the cabin. It was the right size & was just so clean...
4 of 5 stars Reviewed 9 August 2013
Call it a diamond in the rough perhaps(?)...Looks small and quaint from the outside, surprisingly large inside. Old cottage type feel due to style sinks and tables. Nice touches...
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From
€48
Per Night
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1 / 16
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Paris
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Fireplace
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This renovated home still maintains the turn of the century charm of its origins, with modern amenities to make you comfortable. The first floor features a living room with adjoining rustic bar, complete with neon lights and a big speaker for your i-pod, phone or mp3 player to plug into and pump up... View all property information
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From
€205
Per Night
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1 / 13
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Lexington
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Stay in a one-of-a-kind property half-a-block from the Hyatt and Rupp Arena and one block from the Hilton in the heart of downtown Lexington. Every room makes a statement with vibrant artwork, bold architecture and real hardwood, granite & marble flooring throughout. There are 2 bedrooms, one with... View all property information
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From
€78
Per Night
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1 / 4
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Lexington
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This home is located 5 minutes from downtown Lexington and Rupp Arena, 10 minutes from Keeneland and 15 minutes from the Kentucky Horse Park. Whether in town to watch a basketball game, for Keeneland meets, World Equestrian Games or shopping in Hamburg or Fayette Mall this is the perfect location... View all property information
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From
€70
Per Night
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1 / 30
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Lexington
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Space PLEASE READ THE ENTIRE LISTING DETAILS, HOUSE RULES, AND CANCELLATION POLICY BEFORE BOOKING! The home is small but charming at only 728 square feet. Referred to as a “shot-gun” house due to its long and narrow build, this simple architectural structure was brought to America by Haitian... View all property information
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From
€160
Per Night
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1 / 14
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Paris
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Stoner Creek Dock is a private gated 4 acre lot, with a 12ft. elevated waterside cabin. This amazing, private, and serene vacation/romantic getaway is located in the heart of Central Kentucky Horse Country. A private ramp and dock are available to guest with use of two great recreational kayak's or... View all property information
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From
€164
Per Night
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1 / 17
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Lexington
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Great for horse or Bourbon Trail touring, Keeneland Racing, the Rolex Three-Day Event, other Kentucky Horse Park activities, UK Sports and Graduations, across from Lexington Tennis Center. Just 5-10 minutes from the best dining and shopping in Lexington, and 15 minutes from downtown. Two bedroom,... View all property information
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From
€820
Per Night
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1 / 35
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Lexington
6 Bedrooms, 6 Bathrooms, Sleeps 14
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Unbelievable value for your next trip to the Horse Capital of the World! Experience luxury, comfort, and beauty during your stay in Lexington! Perfect for UK Football, UK Basketball, Keeneland, the horse sales, events at the Kentucky Horse Park and the very popular Bourbon Trail! Or just a... View all property information
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From
€103
Per Night
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1 / 6
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Lexington
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Brick Ranch Dwelling on Quiet Court The convenient setting on a very quiet Court provides for additional privacy and security. The Brick Ranch has an eat in kitchen and private patio with gas grill which provides for a relaxing atmosphere. The property is located near great shopping and dining as... View all property information
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From
€267
Per Night
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1 / 19
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Lexington
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Wake Robin Farm is truly a special property with a rich past, restored to make a picturesque setting for your next stay in the Lexington Bluegrass area! The property is set on 19 acres, .6 miles down a gravel drive from US 68, and includes the house with front and back porches, a horse barn, a... View all property information
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From
€72
Per Night
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1 / 13
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Lexington
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Why stay in a hotel? Lexington Relocation Services provides quality, affordable executive housing for short and long term needs. With a wide variety of locations to choose from in and around the beautiful, scenic city of Lexington, Kentucky, our fully furnished apartments are an excellent... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 November 2014
The apartment was exactly as pictured, nice neighborhood. The ease of booking was wonderful and the staff was very friendly and accommodating. Was pleased that it was a very short...
5 of 5 stars Reviewed 3 November 2014
The two bedroom apartment was very spacious, clean and well furnished. Management was very easy to work with and very prompt to respond to any and all questions.
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From
€98
Per Night
View Details
1 / 10
Payment Protection
Lexington
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Why stay in a hotel? Lexington Relocation Services provides quality, affordable executive housing for short and long term needs. With a wide variety of locations to choose from in and around the beautiful, scenic city of Lexington, Kentucky, our fully furnished apartments are an excellent... View all property information
Make Enquiry
4 of 5 stars Reviewed 9 July 2014
The apartment complex was very nice and in a great location in proximity to all the places we wanted to get to in the Lexington area. The two bedroom apartment was nice, neat and...
4 of 5 stars Reviewed 7 July 2014
We picked this place since we were meeting a friend who was also traveling to Lexington. It was much cheaper than us each getting hotel rooms, and since it was a two bedroom, two...
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From
€316
Per Night
View Details
1 / 27
Payment Protection
Lexington
3 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Get back to Nature. Close to Lexington, Relax & Revitalize, Fun for Golfers to come and relax, Family reunions, retreats and more.... 3 Bedroom 3 Bathrooms, Country Home Nestled In The Heart Of The Bluegrass Make our home. . . your home. Located 30 minutes from Lexington, KY. Stay on the 85 acre... View all property information
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5 of 5 stars Reviewed 4 May 2014
Everything was wonderful. The home was very comfortable and lovely and clean. A very friendly and homey environment. Cant wait to stay again.
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From
€144
Per Night
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1 / 7
Payment Protection
Lexington
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Why stay in a hotel? Lexington Relocation Services provides quality, affordable executive housing for short and long term needs. With a wide variety of locations to choose from in and around the beautiful, scenic city of Lexington, Kentucky, our fully furnished apartments are an excellent... View all property information
Make Enquiry
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