Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

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Guest favorite

Train in Lawrenceburg

4.98 out of 5 average rating, 260 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm 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 bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Sep 2 – 9

ﺩ.ﺇ610 per night

Guest favorite

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.

Oct 8 – 15

ﺩ.ﺇ374 per night

Guest favorite

Barn in Mount Eden

4.98 out of 5 average rating, 120 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.

Jun 6 – 13

ﺩ.ﺇ464 per night

Guest favorite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 180 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Jul 9 – 16

ﺩ.ﺇ421 per night

Guest favorite

Guest suite in Louisville

4.98 out of 5 average rating, 179 reviews

Spacious Lower-Level in Quiet Neighborhood

This is a spacious, walk-out lower level with a private entrance. Our quiet neighborhood is 1 1/2 miles from I-265, which means easy access to Louisville or beyond the city to bourbon country. It has a large living area and a fully equipped kitchen. Adventure lovers will like being 5 miles from The Parklands. Downtown Louisville is 20 minutes away. The space has 1 queen bed, 1 double bed, and twin bunk beds. It sleeps 5-6 comfortably. We live upstairs so we are available if needed.

Aug 7 – 14

ﺩ.ﺇ499 per night

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 159 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

Dec 7 – 14

ﺩ.ﺇ360 per night

Guest favorite

Bungalow in Dry Ridge

4.97 out of 5 average rating, 570 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.

Sep 24 – 29

ﺩ.ﺇ415 per night

Guest favorite

Condo in Shelbyville

4.93 out of 5 average rating, 123 reviews

Horses, Bourbon, and More .... Shelbyville Condo

Beautiful condo duplex features 2 bedrooms / 2 full bathrooms, light open floor plan, private entrance with parking at the door.. Close to shopping, expressway, local wineries, bourbon distilleries, horse farms and much more!! Fully Furnished including linens, towels, dishes and more! Work or travel, we welcome you to your home away from home! Located Close to shopping, farms, local interests and I64.. 25 minutes to Louisville, 45 minutes to Lexington.

Aug 2 – 9

ﺩ.ﺇ405 per night

Guest favorite

Cottage in Pleasureville

4.99 out of 5 average rating, 174 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.

Jul 3 – 10

ﺩ.ﺇ449 per night

Guest favorite

Cabin in Mount Eden

4.97 out of 5 average rating, 107 reviews

Bourbon Country Cottage

Newly renovated cottage located in the country. Enjoy amazing views from the porch while enjoying the outdoor patio. Fully furnished to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a well equipped kitchen for cooking. Enjoy exploring the walking trails, creek and the 80 acre property while you stay. Stocked Fishing Pond Check out our other listing too, Bourbon Country Cabin, same property.

Jul 12 – 19

ﺩ.ﺇ567 per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 286 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Sep 2 – 9

ﺩ.ﺇ419 per night

Guest favorite

Home in Bardstown

4.95 out of 5 average rating, 459 reviews

Creekview Farm: Bourbon, Horses, and Sunsets

On this beautiful 19 acre horse farm, you will enjoy beautiful sunrises and sunsets. You will have the country feel while only being 3.5 miles from downtown Bardstown. The airbnb apartment located in the front of the horse barn. It is located behind the main farm house which is a long term rental house. The horses, cats, goats, chickens, and dogs belong to the long term rental tenants.

Aug 31 – Sep 7

ﺩ.ﺇ484 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simpsonville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Simpsonville

Guest favorite

Home in Simpsonville

4.94 out of 5 average rating, 66 reviews

Comfortable sleek home bourbon trail

Feb 15 – 22

ﺩ.ﺇ662 per night

Guest favorite

Farm stay in Simpsonville

4.85 out of 5 average rating, 62 reviews

Farm House - near Bourbon Trail & Pet Friendly

Jul 18 – 25

ﺩ.ﺇ510 per night

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 34 reviews

Spacious suite, country views, pool table, firepit

Nov 27 – Dec 4

ﺩ.ﺇ490 per night

Guest favorite

Farm stay in Simpsonville

4.92 out of 5 average rating, 39 reviews

Spacious Getaway in the Country - 2 Bd, 2 1/2 Bath

Aug 22 – 29

ﺩ.ﺇ634 per night

Guest favorite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 71 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Aug 26 – Sep 2

ﺩ.ﺇ572 per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 31 reviews

Middletown Private Guest House

Jul 27 – Aug 3

ﺩ.ﺇ338 per night

Guest favorite

Apartment in Shelbyville

4.96 out of 5 average rating, 81 reviews

Unique Downtown Studio with an Industrial Vibe

Feb 26 – Mar 5

ﺩ.ﺇ522 per night

Guest favorite

Farm stay in Shelbyville

5.0 out of 5 average rating, 16 reviews

Bourbon trail apartment on horse farm

Dec 28 – Jan 4

ﺩ.ﺇ359 per night

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Quick stats about vacation rentals 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, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
800 reviews
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees

Vacation rentals in Simpsonville

Top-rated vacation rentals in Simpsonville

Train in Lawrenceburg

Apartment in Simpsonville

Barn in Mount Eden

Guesthouse in Hardinsburg

Guest suite in Louisville

Tiny home in La Grange

Bungalow in Dry Ridge

Condo in Shelbyville

Cottage in Pleasureville

Cabin in Mount Eden

Farm stay in Goshen

Home in Bardstown

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Simpsonville vacation rentals

Other great vacation rentals in Simpsonville

Home in Simpsonville

Farm stay in Simpsonville

Guest suite in Shelbyville

Farm stay in Simpsonville

Guesthouse in Shelbyville

Guest suite in Louisville

Apartment in Shelbyville

Farm stay in Shelbyville

Quick stats about vacation rentals in Simpsonville

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore