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Holiday rentals in Jessamine County

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Top-rated holiday rentals in Jessamine County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A spacious living area is furnished with comfortable seating comprised of oversized sofas and armchairs. A rustic wooden coffee table sits at the center, while a stone fireplace is featured prominently along one wall. Large windows offer views of the outdoor landscape.
Cabin in Lexington
4.83 out of 5 average rating, 250 reviews

Rural Kentucky River Palisades Cabin/Past Distilry

Fabulous Cabin & Views of Kentucky River Palisades;Rural Escape 20 minutes S of Lexington;Scenic & Treasured Landscape.View wildlife,Rock Formations,Fall Colors.One mile riverfront,boat ramp&fishing lake;Kayaks&Pontoon Boat avail(xtra fee)Hike & explore 57 acres. History abounds:Site of 1860 Bourbon Distillery;Daniel Boone lived & surveyed from Boone’s Knoll;Loretta Lynn&Dolly Parton performed here;Camp Nelson Civil War National Landmark adjacent;Paul Sawyier’s chosen spot for plein air painting

Top guest favourite
An airy living space is showcased, featuring large windows that invite natural light and provide views of the surrounding fields. Comfortable seating arrangements with a mix of couches and chairs are positioned around a central area rug, highlighting a handcrafted coffee table and a wood stove.
Chalet in Wilmore
4.92 out of 5 average rating, 154 reviews

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

Top guest favourite
A porch overlooks the serene Kentucky River, featuring a wood breakfast bar with counter stools. Rocking chairs provide a cozy seating area, framed by lush greenery and views of the river's banks. Sunlight filters through the trees, enhancing the tranquil setting.
Cottage in Wilmore
4.98 out of 5 average rating, 316 reviews

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

Top guest favourite
A cozy bedroom features a full-sized bed draped in a patterned blue and white coverlet. A bedside lamp and a small table with decorative items complement the space. Natural light filters through a small window, creating a serene ambiance.
Flat in Wilmore
4.97 out of 5 average rating, 375 reviews

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

Top guest favourite
The living room features vaulted ceilings and an open layout. A sectional sofa and a reclining chair offer comfortable seating, while a coffee table sits centrally. Light hardwood flooring and soft wall decor contribute to a bright and airy ambiance. A large TV is mounted on a nearby wall.
Home in Lexington
4.99 out of 5 average rating, 144 reviews

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.

Top guest favourite
Lush green grass frames the scene, with two flowering trees prominently in the foreground. A wooden fence lines the area, leading to a cottage that is partially obscured by the trees. Natural light brightens the surroundings on a clear day.
Guest house in Nicholasville
4.98 out of 5 average rating, 383 reviews

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.

Top guest favourite
Farm stay in Lancaster
5 out of 5 average rating, 213 reviews

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.

Top guest favourite
The exterior of the apartment features a welcoming porch with white railings and hanging flower baskets. A well-maintained lawn with colorful flower beds can be seen, along with a small garden feature. A vehicle is parked in the attached garage to the right.
Flat in Lexington
4.98 out of 5 average rating, 258 reviews

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.

Top guest favourite
A spacious living area features a comfortable sofa adorned with patterned pillows. Natural light illuminates the wooden ceiling and warm tones of the furnishings. A decorative area rug complements a coffee table, while soft lighting from side tables enhances the inviting atmosphere.
Townhouse in Lexington
4.97 out of 5 average rating, 105 reviews

Modern Townhome Close to UK

Welcome to this modern townhome, located in the desirable Chinoe neighborhood. Steps away from Chinoe Shopping Center, you'll find a supermarket, salon, and several restaurants. It's just a quick drive to Kroger Field, and a short drive to the heart of downtown. So whether you're here to place a bet at the Keeneland racetrack, attend a concert at Rupp Arena, tour one of our many bourbon distilleries, or cheer on the Wildcats, you'll find that this townhome is in a convenient location.

Top guest favourite
A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.
Home in Lexington
4.97 out of 5 average rating, 142 reviews

Central Lex Summer Pool Oasis: Hot tub! Games room!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

Guest favourite
Home in Versailles
4.84 out of 5 average rating, 130 reviews

Woodford Stables / Walk to Eckert's Orchard

Welcome to Woodford Stables, your serene retreat nestled amidst rolling hills and picturesque paddocks. This charming farmhouse boasts a modern kitchen, three inviting bedrooms, and two pristine bathrooms. Relax in the cozy living area, or step outside to savor breathtaking views. With horses grazing nearby, it's a tranquil escape. Conveniently located, you can stroll to Eckerts Orchard for a delightful local experience. Ask us about boarding your horses during your stay!!

Top guest favourite
A spacious bedroom is featured with a large, dark bed framed by two bedside lamps. A soft, blue throw blanket adorns the bed. A painting is displayed on the wall above, and a potted plant adds a touch of greenery in the corner.
Home in Wilmore
5 out of 5 average rating, 101 reviews

*KY Charm*Asbury-Lex-Keeneland-King bed-spacious

This spacious, private basement is the perfect lodging for visiting families, commuting students, or out-of-town explorers. Located in a peaceful subdivision in the quaint town of Wilmore, we're within walking distance to Asbury University and Seminary, Centennial Park, hiking trails, and a bustling main street with shops, cafes, and restaurants. We are an easy 20-30 minute drive from Lexington, Keeneland, Rupp Arena, and the Bluegrass Airport. Jess Co Permit #9248

Popular amenities for Jessamine County holiday rentals