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.
Cabin in Louisville
4.95 out of 5 average rating, 300 reviewsCaptain'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
Train in Lawrenceburg
4.98 out of 5 average rating, 250 reviewsBourbon 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
Apartment in Simpsonville
4.98 out of 5 average rating, 130 reviewsRidgecrest 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
Vacation rentals for every style
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Popular amenities for Simpsonville vacation rentals
Other great vacation rentals in Simpsonville
Cottage in Pleasureville
4.99 out of 5 average rating, 174 reviewsThe Cozy Cottage on One Goat Farm
Jun. 23 – 30
Farm stay in Shelbyville
5.0 out of 5 average rating, 30 reviewsCozy Apartment at Red Gate Farm
Jun. 1 – 8
Home in Simpsonville
4.86 out of 5 average rating, 80 reviewsCharming 4 Bedroom classic home bourbon trail!
Sep. 3 – 10
Farm stay in Simpsonville
4.85 out of 5 average rating, 60 reviewsFarm House - near Bourbon Trail & Pet Friendly
Jul. 29 – Aug. 5
Farm stay in Simpsonville
4.95 out of 5 average rating, 38 reviewsSpacious Getaway in the Country - 2 Bd, 2 1/2 Bath
Feb. 13 – 20
Guest suite in Louisville
4.96 out of 5 average rating, 28 reviewsMiddletown Private Guest House
Apr. 22 – 29
Guesthouse in Shelbyville
4.96 out of 5 average rating, 70 reviewsCottage of Eden. Bourbon Trail Stay in Shelby Co.
Aug. 9 – 16
Guest suite in Shelbyville
4.97 out of 5 average rating, 33 reviewsSpacious suite, country views, pool table, firepit
Nov. 2 – 9
Guest suite in Shelbyville
5.0 out of 5 average rating, 60 reviewsComfortable Charm on the Bourbon Trail & 2024 PGA
Jun. 27 – Jul. 4
Apartment in Shelbyville
5.0 out of 5 average rating, 44 reviewsDowntown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Jan. 28 – Feb. 4
Cabin in Louisville
5.0 out of 5 average rating, 65 reviewsHistoric Cabin by Bourbon Trail
Aug. 1 – 8
Home in Shelbyville
5.0 out of 5 average rating, 8 reviewsPool*HOT TUB*Bourbon Trail
Sep. 30 – Oct. 7
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 |
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