Holiday houses in Jessamine County

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

Newly renovated upscale house with high ceilings

Get away and cozy in at this clean and comfortable two bed, two bath private home centrally located in a convenient, quiet neighborhood less than a five-minute walk to Kroger, restaurants, coffee, and a yoga studio. Easily accessible to Fayette Mall and UK by car. Fully equipped kitchen for cooking meals, reclining sofa for relaxing, 65" TV, books and games. One new Sealy king bed and a bunk bed with one double and two twin mattresses (one trundle). Washer and dryer available for your use.

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

Highbridge River Cabin, Private Dock, EV Charger

Relax at the river cabin. Retreat right on the Kentucky River with private dock for easy river access. The cabin has Dual Plug Type 2 EV charger. Cozy cabin on stilts with stone fireplace & porch with table and chairs. Surrounded by nature & beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 mins or less from LEX Airport, Keeneland and Shaker Village. No extra guests without permission, no parties.

Lexington Apt. with parking & private entrance

Lower level apartment with parking and two entrances. Light painted walls, ceiling lighting/fan, plus free washer and dryer. Approximately 10-15 minutes from Bluegrass Airport, 15-20 minutes to the University of Kentucky campus, stadium and 20-25 to Rupp Arena, 10-15 minutes from main entrance to Keeneland Race Track Main entrance, 20-25 minutes to downtown Lexington, 10-15 minutes to shopping mall/restaurants located in mall area, 50 minutes from the ARK ENCOUNTER AND CREATION MUSEUM.

Southern Hospitality! Best location close to UK!

This home has been completely renovated with truly flawless finishes. Approximately 1 mile from all hospitals; UK, Central Baptist, St.Joseph. New kitchen and appliances. Very convenient location to Keeneland, Shopping, and Restaurants. Extremely clean and comfortable living spaces. The living and bed rooms have been equiped with Tv’s. WiFi is included. The shower even has a Bluetooth fan for playing music in the shower. I’ve provided everything to make your trip as enjoyable as possible.

National Historic O'neal Cabin

Originally built during the late 1700’s, this two-story log cabin was restored in 1995. The O'neal Cabin is listed on the National Register of Historic Places. Located in central Kentucky, six miles from historic downtown Lexington, the O’Neal Log Cabin is in the heart of horse country and the bourbon trail. Whether you are looking for a getaway, a place to stay during the horse sales or a retreat while you visit Lexington’s sites, the O'Neal Log Cabin is perfect retreat.

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Cali King beds w/ Koi pond Oasis. 15 min from LEX

Nicholasville's finest short term rental! We recently finished remodeling this spacious ranch home in Nicholasville Ky and are extremely excited to share it with future guests. It looks brand new on the inside and has an awesome oasis in the backyard with water effects/ koi pond. It is close to all the great things to do in Lexington including Keeneland and the University of Kentucky. Mattresses are top of the line and will ensure you have a very comfortable stay.

Coach House at the 1898 Red Bud B & B

Lovingly renovated coach house unit was originally the workshop attached to the back of the coach house. It is a ground floor accommodation with private entrance located behind the main bed & breakfast. We are only two city blocks from Asbury! We make a perfect base to explore the area. The Bourbon Trial, numerous horse farm tours, vineyards, Keeneland, the Horse Park, and historic sites such as Shaker Village of Pleasant Hill. Only 11 miles from Lexington.

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!