Vacation rentals in Kentucky

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Top-rated holiday rentals in Kentucky

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

Guest favourite
Cabin in Louisville
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
7 – 14 Aug
4.96 out of 5 average rating, 297 reviews
Guest favourite
Train in Lawrenceburg
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!
30 Aug – 6 Sept
4.98 out of 5 average rating, 248 reviews
Guest favourite
Home in Stamping Ground
Buffalo Springs Distilling Company
On the Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one bedroom due to the size of the structure. Queen size bed in the bedroom. There’s also a Queen Air Mattress that can be utilized in a pinch for folks that are staying at least a week
29 Dec – 5 Jan
4.97 out of 5 average rating, 594 reviews

Popular amenities for Kentucky holiday rentals

Other great holiday rentals in Kentucky

Guest favourite
Tiny home in Stanton
*NEW* Hot Tub! Tiny Cabin Retreat near RRG
6 – 13 July
4.91 out of 5 average rating, 115 reviews
Guest favourite
Cabin in Lawrenceburg
River Side Cabin - Bourbon Trail - HotTub
6 – 13 Nov
4.96 out of 5 average rating, 164 reviews
Guest favourite
Cabin in Mount Eden
Bourbon Country Cabin
3 – 10 June
4.96 out of 5 average rating, 359 reviews
Guest favourite
Cabin in Dixon
Crouse’s North Ninety Lake House
9 – 16 Aug
4.96 out of 5 average rating, 228 reviews
Guest favourite
Guesthouse in Winchester
Escape and unwind in the country
27 Nov – 4 Dec
4.98 out of 5 average rating, 170 reviews
Guest favourite
Dome in Mount Washington
My Old Kentucky Dome
24 Sept – 1 Oct
4.97 out of 5 average rating, 58 reviews
Guest favourite
Barn in Campbellsville
Peaceful Getaway in the Country
4 – 11 Aug
4.95 out of 5 average rating, 96 reviews
Guest favourite
Cabin in Rogers
Modern A Frame | Red River Gorge
6 – 13 Nov
4.98 out of 5 average rating, 50 reviews
Guest favourite
Dome in Monticello
Dome + HotTub + Escape + Lake
20 – 27 Oct
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cabin in Cadiz
Lake Barkley Treehouse
3 – 10 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cabin in Owenton
The Heron | Lakefront A-Frame, Near Ark Encounter
16 – 23 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Tiny home in Hopkinsville
Romantic, Peaceful Getaway in Nature
24 June – 1 July
5.0 out of 5 average rating, 55 reviews

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