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Search results; Over 1,000 homes

Top guest favourite
Home in Jamestown
The Lodge @ Lake Cumberland Fall/Winter Cabin
4 bedrooms, 9 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Shelbyville
The Rec Farm-Log Cabin, Private Lake & Arcade
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Lawrenceburg
Bourbon Trail Cabin- Sleeps 10-Hot Tub, Firepit
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Cabin in Lebanon
*NEW* Secluded Cabin On Private Lake
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 70 reviews
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Bardstown
NEW Hot Tub • 5BR Estate Near Bourbon Trail
5 bedrooms, 5 beds, 2.5 bathrooms
18–23 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Cabin in Frenchburg
New 4-King Cabin w/ Hot Tub, Cave View, Fire Pit
4 bedrooms, 4 king beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Cabin in Frankfort
6 Private Acres! HotTub~Theater | Gamerm | Arcade
5 bedrooms, 6 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Pine Ridge
Western A Frame with Hot Tub | Red River Gorge
2 bedrooms, 2 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Farm stay in Stamping Ground
Modern Farm Loft
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Home in Shelbyville
High Rollers' Retreat w/pool and Pond
8 bedrooms, 8 beds, 7.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Cabin in Campton
Private pickleball court with hot tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Cabin in Campton
UTV Trailer Parking >3 Kings > Hot Tub > New Build
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cabin in Shepherdsville
Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby
5 bedrooms, 6 beds, 3.5 bathrooms
3–8 Oct
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Home in Jamestown
Romantic Retreat | Fireplaces, Fire Pits & Views
2 bedrooms, 2 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Cabin in Stanton
Private | Hot Tub | Stargazing | Mountain View
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Home in Wellington
Romantic Cabin with Waterfall & Treehouse
2 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.99 out of 5 average rating, 102 reviews