Holiday houses in Simpsonville

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Top-rated holiday rentals in Simpsonville

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Guest favourite

Apartment in Simpsonville

4.98 out of 5 average rating, 130 reviews

Ridgecrest Estate. Comfort and convenience.

A newly renovated 650-sq-ft. upstairs apartment with private entrance. Property sits on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate is an ideal location for enjoying the best of Kentucky in a quiet and peaceful environment. Quick access to I-64 (1/4 mile); 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. No children under 13. Additional guests more than 2, $20 extra per night.

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Home in Shelbyville

4.81 out of 5 average rating, 119 reviews

Parris on Main

Parris on Main Street is the perfect location to enjoy the historic town of Shelbyville and, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite to eat. **Update - brand new ac system installed 7/19/2023 Newly renovated, built in 1942, this house is perfect for a family or group of friends wanting to experience the wonderful places Kentucky has to offer. Right in the middle the Bourbon Trail and about 30 minutes from ChurchIll Downs

Guest favourite

Barn in Mount Eden

4.98 out of 5 average rating, 122 reviews

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs are welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Guest favourite

Tiny home in La Grange

4.98 out of 5 average rating, 164 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Guest favourite

Cottage in Hodgenville

4.98 out of 5 average rating, 147 reviews

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

Guest favourite

Condo in Shelbyville

4.88 out of 5 average rating, 110 reviews

Your Kentucky Home Away From Home

Lovely, renovated Patio Home features 2 bedrooms and 2 full baths – one with a low-entrance shower and one with a full tub. This Open Floor Plan has 1st Floor Entry, front-door parking and 36” doors, making it easily accessible. This home is fully furnished throughout, including a full kitchen with all appliances, dishes, drinkware and silverware, washer and dryer, wall-mounted flat-screen television, tasteful art, linens, towels and more. This is your home away from home!

Guest favourite

Guest suite in Prospect

4.97 out of 5 average rating, 176 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Guest favourite

Bungalow in Dry Ridge

4.97 out of 5 average rating, 579 reviews

The Cute Little House Near The Ark Encounter

The "Little House" is a cute 1 bedroom house located on our farm in a beautiful country setting with 6 acres of outdoor space for relaxing. It is separate from our home and is all yours. It is conveniently located only 8 miles from the Ark Encounter and you only need to make one turn to get there. We have chickens, ducks, rabbits, a horse, and 2 goats. We also have a 1/2 mile nature trail to explore with a scavenger hunt, and a campfire spot with free firewood.

Guest favourite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 453 reviews

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

Guest favourite

Cottage in Pleasureville

4.99 out of 5 average rating, 176 reviews

The Cozy Cottage on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery, it is also in close proximity to a gas station, grocery and library. Located in the heart of an Amish community, you will hear horses and buggies clip-clopping past as you sip your morning coffee. This cottage is on a functioning farm with horses, cats, goats and donkeys, with overnight housing facilities for your own equines as well.

Guest favourite

Cabin in Mount Eden

4.96 out of 5 average rating, 366 reviews

Bourbon Country Cabin

Nestled in the Heart of Bourbon Country sitting on 80 acres of Kentucky woodlands this charming loft style cabin makes a great central location to visit all the local distilleries on the Kentucky Bourbon Trail! Enjoy exploring the walking trails, creek, and the property while you stay in a peaceful cabin in the woods! Check out our other listing too if you have a large group and would like to book both rentals. Bourbon Country Cottage

Guest favourite

Home in Louisville

4.95 out of 5 average rating, 116 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Holiday rentals for every style

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Popular amenities for Simpsonville holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Simpsonville

Guest favourite

Farm stay in Williamstown

4.99 out of 5 average rating, 381 reviews

Mabel’s Cabin

Guest favourite

Farm stay in Shelbyville

4.97 out of 5 average rating, 38 reviews

Cozy Apartment at Red Gate Farm

Guest favourite

Farm stay in Simpsonville

4.93 out of 5 average rating, 42 reviews

Spacious Home with Beautiful Views

Guest favourite

Home in Simpsonville

4.94 out of 5 average rating, 70 reviews

Comfortable sleek home bourbon trail

Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 39 reviews

Spacious suite, country views, pool table, firepit

Guest favourite

Guest suite in Shelbyville

5.0 out of 5 average rating, 65 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

Guest favourite

Farm stay in Simpsonville

4.86 out of 5 average rating, 65 reviews

Farm House - near Bourbon Trail & Pet Friendly

Guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 35 reviews

Middletown Private Guest House

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Quick stats about accommodation in Simpsonville

Total rentals
10 properties
Local attractions
The Old Stone Inn & Tavern, Brick+Mortar Boutique and Coffeehouse and The Lovely Fig
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
10 properties include access to Wi-Fi
Total number of reviews
800 reviews
Nightly prices starting at
$121 AUD before taxes and fees

Holiday houses in Simpsonville

Top-rated holiday rentals in Simpsonville

Apartment in Simpsonville

Home in Shelbyville

Barn in Mount Eden

Tiny home in La Grange

Cottage in Hodgenville

Condo in Shelbyville

Guest suite in Prospect

Bungalow in Dry Ridge

Cabin in Lawrenceburg

Cottage in Pleasureville

Cabin in Mount Eden

Home in Louisville

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Simpsonville holiday rentals

Other great holiday rentals in Simpsonville

Farm stay in Williamstown

Farm stay in Shelbyville

Farm stay in Simpsonville

Home in Simpsonville

Guest suite in Shelbyville

Guest suite in Shelbyville

Farm stay in Simpsonville

Guest suite in Louisville

Quick stats about accommodation in Simpsonville

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Total number of reviews

Nightly prices starting at

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