Holiday rentals in Wilmore

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Top-rated holiday rentals in Wilmore

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

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Top guest favourite
A spacious living area showcases vaulted wooden ceilings and large windows that overlook the scenic landscape. Natural light fills the room, highlighting a leather sofa and comfortable armchair. Decorative elements and artwork are placed on the walls and shelves, enhancing the inviting atmosphere.
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 well-maintained single-story home features a neatly landscaped front yard with green grass and shrubs. Steps lead to the covered entrance, framed by large windows on either side. A driveway displays parked vehicles, surrounded by a grassy area and trees.
Flat in Wilmore
4.98 out of 5 average rating, 374 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

Guest favourite
The exterior of a charming red barn is shown, featuring white accents and a welcoming front door. A wreath adorns the door, and colorful autumn decorations are placed at the base, complemented by lush greenery and a peaceful sunset backdrop.
Barn in Harrodsburg
4.87 out of 5 average rating, 248 reviews

The Beaumont Parlor, 8 miles to Shaker Village

It's rare to find a place that's both historic & one-of-a-kind. That's exactly what you are going to get at The Beaumont Parlor! Formerly an old milk barn & milk parlor for the City of Harrodsburg, this newly restored unit features old world charm & all the modern amenities a guest could ask for. Featuring a King bed, Queen Sleeper Sofa & Full Bathroom. The Owner's have spared no expense and you will find charm at every angle. Guests will be able to walk to Beaumont Inn & Downtown Harrodsburg

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
An outdoor area is visible, featuring a fire pit surrounded by several chairs and a picnic table. Lush green grass is present, complemented by trees in the background. An active railroad bridge looms above, with soft, diffuse light filtering through the clouds.
Cabin in Wilmore
4.95 out of 5 average rating, 165 reviews

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.

Superhost
A charming, dark-colored cottage is set amidst lush greenery. A covered porch is visible at the front, featuring comfortable seating. Flower beds and manicured landscaping enhance the natural surroundings, while tall trees provide shade and tranquility.
Cabin in Versailles
4.88 out of 5 average rating, 98 reviews

Creekside- Bourbon Trail Oasis

Welcome to Creekside, a unique vacation experience nestled in the heart of Versailles, KY. Steeped in nature, Creekside offers majestic views of the river with peaceful waterfalls. In the evening, gather round the crackling fire pit, creating memories under the stars. When you're ready to explore, you'll find downtown Versailles is just a 10-minute drive away. For bourbon lovers, we are just 25 minutes from the famous Woodford Reserve. We now have Starlink wifi to always keep you connected!

Top guest favourite
Train in Lawrenceburg
4.99 out of 5 average rating, 539 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Top guest favourite
A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.
Home in Versailles
4.95 out of 5 average rating, 238 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Top guest favourite
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

Top guest favourite
Home in Nicholasville
4.93 out of 5 average rating, 306 reviews

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. High quality touches on the inside and has a tranqiul 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.

Top guest favourite
A welcoming veranda features several black metal tables and chairs, surrounded by vibrant hanging plants and flower pots filled with red geraniums. The space is framed by white columns and is accessible from the coach house, offering a place to relax outdoors.
Guest house in Wilmore
4.96 out of 5 average rating, 167 reviews

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.

Top guest favourite
Cabin in Lawrenceburg
4.99 out of 5 average rating, 275 reviews

Relax in the hot tub with a view of the River!

Welcome to the Kentucky River Bourbon Cabin! Relax and rejuvenate in this cozy cabin nestled in a wooded setting & on the edge of the Kentucky River! Here you will find peace and serenity in nature with an upfront view of the water. Secluded and private yet still close to stores, restaurants and many tourist attractions such as major distilleries and wineries. Four Roses, Wild Turkey, Woodford Reserve and Buffalo Trace are just a short drive away.

Popular amenities for Wilmore holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Wilmore?

    Wilmore has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Wilmore?

    Experience the best of Wilmore with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Wilmore?

    Yes! Work meets play with ease at over 10 vacation rentals in Wilmore featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Wilmore have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Wilmore. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wilmore have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Wilmore. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wilmore have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Wilmore. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Wilmore

  • Total holiday rentals

    Explore 20 holiday rentals in Wilmore

  • Nightly prices starting at

    Wilmore holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 2,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Wilmore holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wilmore rentals

  • 4.9 Average rating

    Wilmore stays are highly rated by guests – averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Kentucky
  4. Jessamine County
  5. Wilmore