Holiday 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
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 SepIndividual Host,
€ 149 per night
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
9–16 DecIndividual Host,
€ 160 per night
4.97 out of 5 average rating, 594 reviews
Guest favourite
Cottage in Wilmore
River House - Cottage with KY River View & Access
Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.
28 Jul – 4 Aug
€ 136 per night
4.97 out of 5 average rating, 156 reviews

Popular amenities for Kentucky holiday rentals

Other great holiday rentals in Kentucky

Superhost
Earthen home in Stanton
Hobbit Hollow with Hot Tub near Red River Gorge
23–30 AugIndividual Host,
€ 175 per night
4.85 out of 5 average rating, 112 reviews
Guest favourite
Cabin in Elizabethtown
The Cabin- private & cozy 1 queen bed 1 bath
20–27 Nov
€ 114 per night
4.93 out of 5 average rating, 189 reviews
Superhost
Treehouse in Campton
Cliff Dweller: Spend a night Suspended from the R
12–19 AugProfessional Host,
€ 806 per night
4.91 out of 5 average rating, 145 reviews
Guest favourite
Cabin in Dixon
Crouse’s North Ninety Lake House
29 Nov – 6 Dec
€ 154 per night
4.96 out of 5 average rating, 228 reviews
Guest favourite
Bungalow in Dry Ridge
The Cute Little House Near The Ark Encounter
25 Aug – 1 SepIndividual Host,
€ 111 per night
4.97 out of 5 average rating, 558 reviews
Guest favourite
Cabin in Mckee
Mountain Dream Cabin -Fish Pond+Horse Stalls
29 Jul – 5 Aug
€ 82 per night
4.96 out of 5 average rating, 246 reviews
Guest favourite
Barn in Campbellsville
Peaceful Getaway in the Country
4–11 JulIndividual Host,
€ 87 per night
4.95 out of 5 average rating, 96 reviews
Guest favourite
Cabin in Waco
Stunning Cedar Cabin, Hot Tub, Amazing Views!
27 Nov – 4 Dec
€ 157 per night
5.0 out of 5 average rating, 53 reviews
Guest favourite
Cabin in Owenton
The Heron | Lakefront A-Frame, Near Ark Encounter
9–16 Oct
€ 170 per night
5.0 out of 5 average rating, 8 reviews
Superhost
Tiny home in Cub Run
The Camden - Romantic Tiny Cabin Retreat - Hot Tub
1–8 Aug
€ 106 per night
4.79 out of 5 average rating, 75 reviews
Guest favourite
Dome in Mount Washington
My Old Kentucky Dome
24 Sep – 1 Oct
€ 503 per night
4.97 out of 5 average rating, 58 reviews
Guest favourite
Home in Magnolia
Magnolia Pines Farmhouse in quiet country setting
23–30 Aug
€ 115 per night
4.96 out of 5 average rating, 68 reviews

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