Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

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

Guest favourite

Cabin in Louisville

4.95 out of 5 average rating, 300 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

Aug. 15 – 22

$430 CAD per night
Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 250 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!

Aug. 30 – Sep. 6

$225 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.

Sep. 6 – 13

$162 CAD per night

Popular amenities for Simpsonville vacation rentals

Other great vacation rentals in Simpsonville

Guest favourite

Cottage in Pleasureville

4.99 out of 5 average rating, 174 reviews

The Cozy Cottage on One Goat Farm

Jun. 23 – 30

$168 CAD per night
Guest favourite

Farm stay in Shelbyville

5.0 out of 5 average rating, 30 reviews

Cozy Apartment at Red Gate Farm

Jun. 1 – 8

$150 CAD per night
Superhost

Home in Simpsonville

4.86 out of 5 average rating, 80 reviews

Charming 4 Bedroom classic home bourbon trail!

Sep. 3 – 10

$294 CAD per night
Guest favourite

Farm stay in Simpsonville

4.85 out of 5 average rating, 60 reviews

Farm House - near Bourbon Trail & Pet Friendly

Jul. 29 – Aug. 5

$221 CAD per night
Guest favourite

Farm stay in Simpsonville

4.95 out of 5 average rating, 38 reviews

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

Feb. 13 – 20

$290 CAD per night
Guest favourite

Guest suite in Louisville

4.96 out of 5 average rating, 28 reviews

Middletown Private Guest House

Apr. 22 – 29

$148 CAD per night
Guest favourite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 70 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Aug. 9 – 16

$215 CAD per night
Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 33 reviews

Spacious suite, country views, pool table, firepit

Nov. 2 – 9

$192 CAD per night
Guest favourite

Guest suite in Shelbyville

5.0 out of 5 average rating, 60 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

Jun. 27 – Jul. 4

$210 CAD per night
Guest favourite

Apartment in Shelbyville

5.0 out of 5 average rating, 44 reviews

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

Jan. 28 – Feb. 4

$169 CAD per night
Guest favourite

Cabin in Louisville

5.0 out of 5 average rating, 65 reviews

Historic Cabin by Bourbon Trail

Aug. 1 – 8

$307 CAD per night
Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 8 reviews

Pool*HOT TUB*Bourbon Trail

Sep. 30 – Oct. 7

$619 CAD per night

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

760 reviews

Nightly prices starting at

$109 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Shelby County
  5. Simpsonville