Vintage Bourbon Haven
Vintage Bourbon Haven
Vintage Bourbon Haven
Vintage Bourbon Haven
Vintage Bourbon Haven

Vintage Bourbon Haven

3 bedrooms·2½ baths
Springfield • Kentucky
5(69 reviews)
$140 – $385/ night(excl. fees & taxes)
The Lucky House
The Lucky House
The Lucky House
The Lucky House
The Lucky House

The Lucky House

3 bedrooms·2 baths
Erlanger • Kentucky
4.88(74 reviews)

$569.43 USD total for 3 nights

Jan 11 – 14, 2027

Moveable TV for upstairs
Nolin Gnome Home- A-Frame Cabin
Welcome to the GNOME HOME!! It's always 5:00 when you are here! But please be respectful of the neighbors, and please no glass containers because they're HEAVY in the trash, and broken glass outside is VERY difficult to clean up. TIA!
Nolin Gnome Home- A-Frame Cabin
Nolin Gnome Home- A-Frame Cabin

Nolin Gnome Home- A-Frame Cabin

4 bedrooms·1 bath
Cub Run • Kentucky
5(29 reviews)

$665.00 USD total for 3 nights

Sep 22 – 25, 2026

Lakeside @ The Harvesters: 1 LVL, Dock, Fish, ARK
FRONT VIEW OF OUR LAKESIDE HOME!
Lakeside @ The Harvesters: 1 LVL, Dock, Fish, ARK
Lakeside @ The Harvesters: 1 LVL, Dock, Fish, ARK
Lakeside @ The Harvesters: 1 LVL, Dock, Fish, ARK

Lakeside @ The Harvesters: 1 LVL, Dock, Fish, ARK

4 bedrooms·2½ baths
Crittenden • Kentucky
4.79(52 reviews)

$790.06 USD total for 3 nights

Sep 28 – Oct 1, 2026

Front of cabin.
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
4-person hot tub.
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Wood-burning fire pit at night all lit up. Chairs for 14 people.

Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!

4 bedrooms·2 baths
Stanton • Kentucky
5(15 reviews)

$1,028.50 USD total for 3 nights

Jan 1 – 4, 2027

Hot Tub Games Firepit Historic Luxe Bourbon Trail
Stay productive and relaxed with a dedicated workspace featuring a leather office chair and a cozy corner swivel chair, perfect for work or unwinding.
Our favorite space in the house features an arcade, a record player, cards, a poker set, and various games, all complemented by a bartender kit and glassware for a complete entertainment experience.
From the basics to the extras, we've got you covered! Fridge, electric stovetop, oven, dishwasher, microwave, toaster, crockpot, blender, hand mixer
Challenge friends and family on our Pac-Man arcade, perfect for all ages. Relive memories or share the thrill of classic gaming during your stay!

Hot Tub Games Firepit Historic Luxe Bourbon Trail

3 bedrooms·2½ baths
Frankfort • Kentucky
4.98(49 reviews)
$194 – $753/ night(excl. fees & taxes)
Secluded・Speakeasy・Sauna・Cigar Shed・Hot Tub
Welcome to The Bourbon Exhale—a beautifully renovated farmhouse where rustic charm meets refined comfort. Set on over an acre of peaceful Kentucky countryside, this inviting retreat offers privacy, style & a warm welcome from the moment you arrive.
Gather, sip, and relax after a day on the Bourbon Trail—the covered deck features cozy seating around the fire, an outdoor dining area, a bubbling hot tub, and a barrel sauna made for unwinding in good company.
Kick back or turn in—this stylish basement sofa easily transforms into a comfy sleeper.
Stretch out on the luxe king bed wrapped in organic cotton Quince linen, then wake to gentle light and peaceful views that make sleeping in irresistible.

Secluded・Speakeasy・Sauna・Cigar Shed・Hot Tub

3 bedrooms·3 baths
Lawrenceburg • Kentucky
5(30 reviews)

$1,294.70 USD total for 3 nights

Sep 27 – 30, 2026

Louisville Louvre
Louisville Louvre
Louisville Louvre
Utilize our home office setup, equipped for any remote work or schooling needs
Louisville Louvre

Louisville Louvre

3 bedrooms·2 baths
Louisville • Kentucky
5(1 review)

$6,250.00 USD total for 30 nights

Oct 31 – Nov 30, 2026

The Hilton House | The Loft image 1
The Hilton House | The Loft image 2
Living/ work space
The Hilton House | The Loft image 4
This daybed functions as seating for the main living space, or serves as a third bed/ bedroom for added options during your stay!

The Hilton House | The Loft

3 bedrooms·1 bath
Ashland • Kentucky

$450.50 USD total for 3 nights

Sep 22 – 25, 2026

Newly Remodeled Condo in Historic Lowertown
Newly Remodeled Condo in Historic Lowertown
Newly Remodeled Condo in Historic Lowertown
Newly Remodeled Condo in Historic Lowertown
Newly Remodeled Condo in Historic Lowertown

Newly Remodeled Condo in Historic Lowertown

1 bedroom·1 bath
Paducah • Kentucky
4.78(59 reviews)
$82/ night(excl. fees & taxes)
The Hilton House | Central Park Retreat image 1
The Hilton House | Central Park Retreat image 2
The Hilton House | Central Park Retreat image 3
The Hilton House | Central Park Retreat image 4
The Hilton House | Central Park Retreat image 5

The Hilton House | Central Park Retreat

2 bedrooms·1 bath
Ashland • Kentucky

$560.20 USD $520.19 USD total for 3 nights

Jan 15 – 18, 2027

Soak in the private hot tub under the stars after a day of adventure.
Welcome to Rocky Hill Retreat! Nestled among mature trees, this cozy country cottage is your perfect Kentucky getaway.
Gather around the dining table and enjoy a fully equipped kitchen with everything you need to prepare meals
Bright, open kitchen with modern appliances and seating for family meals or game nights.
Unwind in the inviting living room with a Smart TV, comfortable seating, and fun games for everyone.

Rocky Hill Retreat

2 bedrooms·1 bath
Rocky Hill • Kentucky
5(4 reviews)
$115 – $161/ night(excl. fees & taxes)
Lake Cumberland • Sleeps 16 • Mancave • Lake Views
Stone lakeside ranch with blue roof, garage, and relaxing front porch.
Bright kitchen with stainless appliances and ample counter space
Lake Cumberland • Sleeps 16 • Mancave • Lake Views
Twilight horizon views from a private, wooded deck—serene escape.

Lake Cumberland • Sleeps 16 • Mancave • Lake Views

4 bedrooms·3 baths
Somerset • Kentucky
5(41 reviews)
$244 – $1,356/ night(excl. fees & taxes)
The Lucky Lodge- Private RR Gorge Couple's Getaway
The Lucky Lodge- Private RR Gorge Couple's Getaway
The Lucky Lodge- Private RR Gorge Couple's Getaway
Such an inviting place to sit.
The Lucky Lodge- Private RR Gorge Couple's Getaway

The Lucky Lodge- Private RR Gorge Couple's Getaway

2 bedrooms·1 bath
Burkesville • Kentucky
4.85(27 reviews)

$470.72 USD total for 3 nights

Sep 22 – 25, 2026

Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
Expansive covered outdoor living space featuring deep-seat sectional lounge chairs, egg swings, and outdoor dining.
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub

Bourbon Trail Estate | 6BR | Pickleball | Hot Tub

6 bedrooms·4½ baths
Chaplin • Kentucky

$2,141.86 USD total for 3 nights

Sep 27 – 30, 2026

Rainbow Ranch Home: No Step Entry in Williamstown!
Rainbow Ranch Home: No Step Entry in Williamstown!
Rainbow Ranch Home: No Step Entry in Williamstown!
Rainbow Ranch Home: No Step Entry in Williamstown!
Rainbow Ranch Home: No Step Entry in Williamstown!

Rainbow Ranch Home: No Step Entry in Williamstown!

4 bedrooms·2½ baths
Williamstown • Kentucky
4.97(29 reviews)

$769.48 USD total for 3 nights

Sep 22 – 25, 2026

Charming 2 bedroom Home
Charming 2 bedroom Home
Charming 2 bedroom Home
Charming 2 bedroom Home
Charming 2 bedroom Home

Charming 2 bedroom Home

2 bedrooms·1 bath
Paducah • Kentucky
$124/ night(excl. fees & taxes)
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses

Deck+Grill | View | 4BR | Wild Turkey | Four Roses

4 bedrooms·2½ baths
Lawrenceburg • Kentucky

$760.00 USD total for 3 nights

Sep 22 – 25, 2026

The Gathering Place: 5bed Family Friendly near ARK
The Gathering Place: 5bed Family Friendly near ARK
The Gathering Place: 5bed Family Friendly near ARK
The Gathering Place: 5bed Family Friendly near ARK
The Gathering Place: 5bed Family Friendly near ARK

The Gathering Place: 5bed Family Friendly near ARK

5 bedrooms·3 baths
Dry Ridge • Kentucky
5(1 review)

$802.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Welcome to your Lake Cumberland retreat—sunset views and room for 14.
Lakeview Lodge • Sleeps 14 • Game Room • Fire Pit
Lakeview Lodge • Sleeps 14 • Game Room • Fire Pit
Lakeview Lodge • Sleeps 14 • Game Room • Fire Pit
See how the river bends—true lakefront living at its finest.

Lakeview Lodge • Sleeps 14 • Game Room • Fire Pit

5 bedrooms·2 baths
Bronston • Kentucky
$254 – $1,203/ night(excl. fees & taxes)
4BR Lake Cumberland Cabin | Hot Tub, Near Boat Ramps
4BR Lake Cumberland Cabin | Hot Tub, Near Boat Ramps
4BR Lake Cumberland Cabin | Hot Tub, Near Boat Ramps
4BR Lake Cumberland Cabin | Hot Tub, Near Boat Ramps
4BR Lake Cumberland Cabin | Hot Tub, Near Boat Ramps

4BR Lake Cumberland Cabin | Hot Tub, Near Boat Ramps

4 bedrooms·3 baths
Jamestown • Kentucky

$1,113.63 USD total for 3 nights

Sep 28 – Oct 1, 2026

Dark skies most unique feature includes the largest rooftop deck in the area!
Dark Skies
The best sunsets from the rooftop of Dark Skies
Dark Skies
Dark Skies

Dark Skies

2 bedrooms·1½ baths
Campton • Kentucky
Garden on Capital-Bourbon & Horse Country
Quiet and charming home walking distance to so much!
Garden on Capital-Bourbon & Horse Country
Garden on Capital-Bourbon & Horse Country
Garden on Capital-Bourbon & Horse Country

Garden on Capital-Bourbon & Horse Country

2 bedrooms·1 bath
Frankfort • Kentucky
$138 – $613/ night(excl. fees & taxes)
Step into a vibrant and stylish kitchen that exudes coolness, featuring a contemporary design that is sure to impress.
This freestanding masterpiece is a celebration of design, its smooth porcelain surface adorned with gleaming, polished chrome fixtures that harken back to a bygone era.
Our bedroom, adorned with pristine white sheets, is a serene oasis where tranquility and comfort merge into a haven of restful reprieve.
Experience the epitome of comfort with a sleep-worthy sofa that offers both relaxation and a cozy chilling experience.
Loft on Capital - Ideally located to Distilleries

Loft on Capital - Ideally located to Distilleries

1 bedroom·1 bath
Frankfort • Kentucky

$654.85 USD total for 3 nights

Sep 26 – 29, 2026