Holiday rentals in Simpsonville

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Top-rated holiday rentals in Simpsonville

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

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Guest favourite

The spacious living area showcases original wooden beams and exposed brick walls. A round plush couch surrounds a glass coffee table, while a projector hangs above for movie nights. The vibrant area rug adds a cozy touch to the open layout.

Loft in Shelbyville

4.98 out of 5 average rating, 123 reviews

Close to Buffalo Trace/Transpo available-Must See

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

Top guest favourite

A spacious studio apartment is showcased with a comfortable bed adorned in a black and white checkered pattern, complemented by red accents. A cozy seating area features a light-colored sofa. Natural light illuminates the wood flooring, and decorative elements enhance the inviting layout.

Flat in Simpsonville

4.98 out of 5 average rating, 141 reviews

Ridgecrest Estate. Comfort and Convenience.

Enjoy the best of Kentucky in our immaculate, 650-sq-ft. upstairs studio apartment with private entrance on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate offers a quiet, peaceful environment in the heart of the Bourbon Trail. Quick access to I-64 (1/2 mile), 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. Sleeps two. No children under 13. Pool access not included with reservation.

Top guest favourite

A cozy front porch features woven chairs arranged around a small table, inviting relaxation. Lush green ferns are placed in terracotta pots, complementing the rustic wooden beams and the log cabin's natural surroundings.

Cabin in La Grange

4.97 out of 5 average rating, 138 reviews

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

Top guest favourite

The exterior of a single-story brick house is shown under a clear blue sky. A driveway leads to a two-car garage, and a landscaped front yard features green grass and shrubs. A large window above the entrance highlights the architectural design.

Home in Shelbyville

4.97 out of 5 average rating, 64 reviews

Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio

A great centrally located 4 BR 2.5 Bath (6 beds) dog-friendly house near downtown Shelbyville! Located in a cul-de-sac on a quiet street in a family friendly neighborhood 6 miles from Bulleit Bourbon, 3 miles to Jeptha Creed Distillery, and 1 mile from the Shelbyville Horse Show. Fully updated & stocked, coffee pot (K-cups or ground), washer/dryer, & 5 smart TVs. This rental has everything you need and proximity to Churchill Downs, multiple Bourbon Trail distilleries, Louisville, and Frankfort!

Top guest favourite

A spacious, single-story residence is showcased, featuring a welcoming porch with seating. The driveway accommodates multiple vehicles and is framed by well-maintained landscaping. The exterior is a mix of brick and siding, with a gently sloping yard and a wooden staircase leading to the entrance.

Home in Louisville

4.96 out of 5 average rating, 54 reviews

Entire House in Middletown - Trailers/RVs access

Make some memories at this unique and family-friendly place. Enjoy your morning coffee or spend your evening with family and friends on the rear deck overlooking the peaceful, spacious 2-acres, park-like view. The property is conveniently located close to everything including restaurants, supermarkets, amusement park, indoor malls, outlet mall. The home features 3 bedrooms, 2.5 baths, with granite countertops throughout. Enjoy your indoor space with wifi, tv's. Sleeps 6 to 8. Can park RV's.

Top guest favourite

A hot tub is situated under an awning, surrounded by soft, white curtains that provide privacy. The bubbling water reflects the greenery of trees beyond, enhancing the serene atmosphere of the outdoor area.

Cottage in Simpsonville

5.0 out of 5 average rating, 68 reviews

KY Cottage near Bourbon, Expo & Horse Park|Hot Tub

Welcome to Miles Around KY Cottage with a relaxing hot tub! Your cozy "Goldilocks" home base,perfectly placed for exploring! Easy drives to Louisville, Frankfort, Bardstown Lexington and more. Shopping: Outlets just 1 mile away! Parking: 4 cars and up to 20ft trailers -message us . Note: We are building our dream home 1/2 acre away, far enough to keep your privacy, but we do share the driveway. Children welcome at your discretion- home is not baby proofed. See house rules for more info.

Top guest favourite

The farmhouse is set against a vibrant sunset, illuminating the sky with shades of orange and pink. The white two-story structure features a welcoming porch, surrounded by lush green grass and a rural landscape.

Farm stay in Simpsonville

4.89 out of 5 average rating, 101 reviews

Farm House - near Bourbon Trail & Pet Friendly

Late 1800's farm house on a 155 acre working family farm located in the heart of the Bourbon Trail. It is a unique experience to stay on our farm where we raise non-GMO corn that goes into producing bourbons here in Kentucky. The farm is rural and private, but convenient to Louisville, distilleries and many other local attractions. We are located only 10 minutes from the Gene Snyder Freeway in Louisville and 10 minutes from the Outlet Shops of the Bluegrass and 15 minutes from Shelbyville.

Top guest favourite

The exterior of Sabre Hill Farm is captured, showcasing a multi-story, dark blue and wooden house surrounded by greenery. A gated entrance leads to a tree-lined driveway. A sign with the farm's name and address is prominently displayed in the foreground.

Farm stay in Simpsonville

5.0 out of 5 average rating, 56 reviews

4BR Farm~Bourbon Trail~private heated pool~horses

Sabre Hill Farm house rental is the perfect place to immerse yourself in the relaxing sounds of nature. On the 25 acres you will find all the comforts of home on a farm with horses, goats and mules. It is ideally positioned as home base for both indoor & outdoor activities including Derby & Horse Events, group gatherings &/or bourbon tours. Between activities unwind on the veranda or pool overlooking the horse paddocks. Saltwater Pool May thru Oct. heated 85*. Wifi is NOT fast here

Guest favourite

A hot tub filled with water sits invitingly, surrounded by greenery and a clear sky. A glass of whiskey rests on the edge, complementing the tranquil setting. The bubbles within the hot tub suggest relaxation awaits in this outdoor space.

Home in Simpsonville

4.92 out of 5 average rating, 78 reviews

*Distilleries close by* Hot tub*Firepit

Welcome to this beautiful, new 4 bedroom, 3.5 bathroom home ready to be the place for your bourbon trail stay! Centrally located just outside of Louisville. This home is less than 30 minutes from downtown Louisville where you can enjoy multiple distilleries, the Louisville Slugger Museum & Factory, Churchill Downs, the Fair & Expo, and just a short drive to Four Roses, Lexington and so much more! Air Hockey, hot tub, Golden Tee and fire pit are all waiting for your group to enjoy!

Guest favourite

A single-story home with a welcoming front porch is surrounded by well-maintained lawns and shrubs. The structure features multiple windows and a gabled roof, with warm evening light illuminating the exterior. A paved path leads to the entrance, enhancing accessibility.

Home in Simpsonville

4.98 out of 5 average rating, 40 reviews

The Haven Simpsonville* Bourbon Trail* 3 bed/3bath

Welcome to the Haven in the heart of Simpsonville, KY, the Saddlebred capital of the world. Located within walking distant of local eateries, shopping, & coffee. The Haven is close to local Distilleries, centrally located between Louisville and Lexington, on the Bourbon Trail, and less than 2 miles from The Outlet Shoppes of the Bluegrass. This spacious 3 bedroom, 3 bath home was designed to be a place of peace & comfort and is perfect for both families and group trips alike.

Guest favourite

The spacious living area features large windows allowing ample natural light. Elegant details include high ceilings and exposed brick walls. A plush sofa is arranged around a coffee table, while a dining area with a wooden table is visible in the background.

Loft in Shelbyville

4.92 out of 5 average rating, 51 reviews

The Lucky Penny Downtown Loft - Central Location!

Experience timeless charm in this beautifully renovated mid-19th century Airbnb in the heart of Shelbyville. With soaring 14 ft ceilings, this historic gem combines classic architecture with modern amenities. Centrally located, it offers convenient access to local attractions, dining, and shopping. Enjoy a blend of elegance and comfort in a space that honors its rich heritage while providing all the contemporary conveniences you need for a memorable stay.

Guest favourite

An open-plan kitchen and living area features modern appliances, including a sleek stove under a black hood. A round wooden dining table is surrounded by four upholstered chairs. A green couch is positioned near a textured area rug, with natural light illuminating the space through large windows.

Home in Shelbyville

4.89 out of 5 average rating, 79 reviews

Quiet Downtown Maple Cottage Gem

Welcome to our charming Maple Cottage in the heart of a peaceful downtown neighborhood. This 3-bedroom, 1-bathroom home has undergone a complete remodel, ensuring a cozy and comfortable stay in Shelbyville. Whether you're here for a weekend getaway or an extended stay, this cottage offers all the amenities you need. The fully fenced backyard offers privacy and space for relaxation and smores over the fire pit. Your Shelbyville adventure begins here!