Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

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Guest favourite

Cabin in Louisville

4.95 out of 5 average rating, 302 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. 3 – 10

$434 CAD per night

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.

Oct. 7 – 14

$165 CAD per night

Guest favourite

Barn in Mount Eden

4.98 out of 5 average rating, 119 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. 8 – 15

$195 CAD per night

Guest favourite

Tiny homes 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

Nov. 7 – 14

$155 CAD per night

Guest favourite

Condo in Shelbyville

4.89 out of 5 average rating, 109 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!

Aug. 18 – 25

$189 CAD per night

Guest favourite

Guest suite in Prospect

4.97 out of 5 average rating, 169 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.

Jun. 19 – 26

$222 CAD per night

Guest favourite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 442 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.

Mar. 26 – Apr. 2

$172 CAD per night

Guest favourite

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. 24 – 31

$172 CAD per night

Guest favourite

Cabin in Mount Eden

4.96 out of 5 average rating, 361 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. 28 – Jul. 5

$274 CAD per night

Guest favourite

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....

Aug. 10 – 17

$182 CAD per night

Superhost

Home in Simpsonville

4.87 out of 5 average rating, 85 reviews

Charming 4 Bedroom classic home bourbon trail!

Comfortable, newly furnished home located in downtown Simpsonville. This is brand new to AirBnB. Whether you are going down the Bourbon trail or you just want to be near I64 and Louisville, this home is the place for you. Fun, homey well decorated this place offers family fun with Fire pit, backyard and patio. High speed 300mb internet for those workers on the go.

Feb. 27 – Mar. 6

$283 CAD per night

Guest favourite

Farm stay in La Grange

4.95 out of 5 average rating, 625 reviews

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage 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. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

Jan. 2 – 9

$238 CAD 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 favourite

Farm stay in Simpsonville

4.85 out of 5 average rating, 62 reviews

Farm House - near Bourbon Trail & Pet Friendly

Aug. 6 – 13

$224 CAD per night

Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 34 reviews

Spacious suite, country views, pool table, firepit

Jan. 22 – 29

$195 CAD per night

Guest favourite

Farm stay in Simpsonville

4.92 out of 5 average rating, 39 reviews

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

Jun. 20 – 27

$287 CAD per night

Guest favourite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 71 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Jun. 18 – 25

$218 CAD per night

Guest favourite

Guest suite in Shelbyville

5.0 out of 5 average rating, 61 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

Jun. 28 – Jul. 5

$236 CAD per night

Guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 30 reviews

Middletown Private Guest House

Aug. 2 – 9

$150 CAD per night

Guest favourite

Farm stay in Shelbyville

5.0 out of 5 average rating, 16 reviews

Bourbon trail apartment on horse farm

Jun. 4 – 11

$150 CAD per night

Guest favourite

Apartment in Shelbyville

5.0 out of 5 average rating, 45 reviews

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

Feb. 10 – 17

$219 CAD 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
$110 CAD before taxes and fees

Vacation rentals in Simpsonville

Top-rated vacation rentals in Simpsonville

Cabin in Louisville

Apartment in Simpsonville

Barn in Mount Eden

Tiny homes in La Grange

Condo in Shelbyville

Guest suite in Prospect

Cabin in Lawrenceburg

Cottage in Pleasureville

Cabin in Mount Eden

Farm stay in Goshen

Home in Simpsonville

Farm stay in La Grange

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Simpsonville vacation rentals

Other great vacation rentals in Simpsonville

Farm stay in Simpsonville

Guest suite in Shelbyville

Farm stay in Simpsonville

Guesthouse in Shelbyville

Guest suite in Shelbyville

Guest suite in Louisville

Farm stay in Shelbyville

Apartment 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