Vacation rentals in Simpsonville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Simpsonville

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cabin in Louisville

4.95 out of 5 average rating, 305 reviews

Captain's Cabin:Historic Romantic by Bourbon Trail

Your own log cabin on a wooded hillside overlooking a private lake with gourmet breakfast served to your door (on weekends)! It's been the location for Lifetime and Hallmark movies! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience

Dec 9 – 16

ﺩ.ﺇ1,009 per night

Guest favorite

Farm stay in Simpsonville

4.86 out of 5 average rating, 63 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.

Jun 9 – 16

ﺩ.ﺇ522 per night

Guest favorite

Guest suite in Shelbyville

5.0 out of 5 average rating, 65 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

You’ll be charmed by this adorable place to stay, close to the interstate, making travel to Valhalla Golf Course, bourbon distilleries, Churchill Downs, and other attractions in nearby Louisville a breeze. We are in a beautiful rural setting, just right for relaxing. Our space has its own private entrance with a comfortable living room and private bathroom downstairs, and features a loft with queen bed and desk. There are a microwave, coffee maker, and fridge available for your convenience.

Jun 3 – 10

ﺩ.ﺇ498 per night

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 35 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

Aug 22 – 29

ﺩ.ﺇ485 per night

Guest favorite

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.

Sep 4 – 11

ﺩ.ﺇ459 per night

Guest favorite

Tiny home in La Grange

4.98 out of 5 average rating, 161 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 8 – 15

ﺩ.ﺇ368 per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 174 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.

Jul 21 – 28

ﺩ.ﺇ542 per night

Guest favorite

Condo in Shelbyville

4.94 out of 5 average rating, 124 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 5 – 12

ﺩ.ﺇ426 per night

Guest favorite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 449 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.

Jan 22 – 29

ﺩ.ﺇ422 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 23 – 30

ﺩ.ﺇ409 per night

Guest favorite

Cabin in Mount Eden

4.96 out of 5 average rating, 364 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

Jun 24 – Jul 1

ﺩ.ﺇ643 per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 290 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....

Jan 16 – 23

ﺩ.ﺇ428 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, 68 reviews

Comfortable sleek home bourbon trail

Jan 21 – 28

ﺩ.ﺇ674 per night

Guest favorite

Farm stay in Simpsonville

4.93 out of 5 average rating, 41 reviews

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

Jun 2 – 9

ﺩ.ﺇ533 per night

Guest favorite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 73 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Jul 24 – 31

ﺩ.ﺇ538 per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 33 reviews

Middletown Private Guest House

Oct 9 – 16

ﺩ.ﺇ345 per night

Guest favorite

Apartment in Shelbyville

5.0 out of 5 average rating, 45 reviews

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

May 14 – 21

ﺩ.ﺇ453 per night

Guest favorite

Farm stay in Shelbyville

5.0 out of 5 average rating, 18 reviews

Bourbon trail apartment on horse farm

Feb 18 – 25

ﺩ.ﺇ366 per night

Guest favorite

Home in La Grange

4.91 out of 5 average rating, 87 reviews

Little Blue Cottage on Main Street, La Grange KY

Oct 24 – 31

ﺩ.ﺇ531 per night

Guest favorite

Cabin in Louisville

5.0 out of 5 average rating, 81 reviews

Historic Cabin by Bourbon Trail

Oct 10 – 17

ﺩ.ﺇ726 per night

Show all

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

Cabin in Louisville

Farm stay in Simpsonville

Guest suite in Shelbyville

Guest suite in Shelbyville

Barn in Mount Eden

Tiny home in La Grange

Guest suite in Prospect

Condo in Shelbyville

Cabin in Lawrenceburg

Cottage in Pleasureville

Cabin in Mount Eden

Farm stay in Goshen

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

Guesthouse in Shelbyville

Guest suite in Louisville

Apartment in Shelbyville

Farm stay in Shelbyville

Home in La Grange

Cabin in Louisville

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