839 homes

Cottage in Versailles
Riverside Rye-bourbon themed water front cottage
4 beds
Oct 17 – 22
$200 per night
Superhost
Home in Frankfort
Charming house in the heart of Frankfort.
2 queen beds
Oct 10 – 15
$165 per night
Superhost
Home in Lexington
Spacious *ADA access 3br 2 bath quiet home
3 beds
Oct 9 – 14
$99 per night
Condo in Frankfort
Capital City Condo #4
2 beds
Nov 7 – 12
$65 per night
Apartment in Frankfort
9-South Frankfort Bourbon Trail Apartment
2 single beds
Oct 29 – Nov 3
$88 per night, originally $110
Superhost
Cottage in Lawrenceburg
Cottage #3 Gorgeous 2 bed Bourbon Trail *Prebook*
2 beds
Oct 24 – 29
$191 per night
Superhost
Apartment in Lexington
The Loft @ West Second
2 queen beds
Oct 16 – 21
$69 per night, originally $194
Superhost
Home in Frankfort
The Manor House
8 beds
Nov 6 – 12
$180 per night
Home in Frankfort
The Bourbon Zone Entire Craftsman House
6 beds
Nov 20 – 25
$260 per night
Superhost
Home in Shelbyville
Hardesty Cottage (Hosted By One Goat Farm)
2 beds
Oct 31 – Nov 5
$103 per night
Superhost
Home in Frankfort
Morrow House-Newly Renovated Farmhouse 3 bedrooms
4 beds
Oct 23 – 28
$152 per night
Superhost
Townhouse in Frankfort
Historic Frankfort Properties
3 beds
Nov 27 – Dec 2
$275 per night
Superhost
Home in Lawrenceburg
Bourbon Trail*DERBY 23’- just 45 mins to Lou!
3 beds
Oct 30 – Nov 4
$280 per night
Superhost
Cabin in Mount Eden
Bourbon Country Cabin
2 beds
Nov 21 – 26
$156 per night
Superhost
Home in Lexington
Private for 4 No cleaning fee Discounts up to 20%
2 queen beds
Oct 28 – Nov 2
$80 per night
Home in Shelbyville
KY Bourbon Trail, King Bed, FirePit, By Louisville
2 beds
Oct 6 – 11
$193 per night
Superhost
Home in Frankfort
The Julep - Cozy yet spacious, near local hotspots
6 beds
Nov 13 – 18
$345 per night
Superhost
Apartment in Lexington
"THE NELSON" Apt/ 10 Min to Downtown or Keeneland
3 beds
Nov 7 – 13
$60 per night
Loft in Frankfort
Downtown Frankfort Bourbon Trail Loft
4 beds
Oct 9 – 14
$220 per night
Superhost
Home in Frankfort
Capital City Bourbon Trail Loft
5 beds
Oct 23 – 28
$400 per night
Superhost
Private room in Lexington
Lexington Home for Bluegrass Adventures
2 beds
Oct 23 – 28
$45 per night
Superhost
Home in Frankfort
Frankfort Bourbon Trail/Horse Country Hacienda
5 beds
Oct 9 – 14
$207 per night
Farm stay in Frankfort
Kamp Kessa at Cedar Fire Farm: A Nature Retreat
9 beds
Oct 4 – 9
$89 per night
Home in Georgetown
Comfy 2 bedroom house. 1 bathroom. Will sleep up 5
4 beds
Oct 9 – 14
$99 per night