Outside patio swing/firepit area with pavilion.
Living room.
Stubborn German House of Bourbon, Lawrenceburg, KY
Living room.
Fully stocked kitchen with plates/utensils/serving utensils, pots/pans, coffee maker and supplies.

Stubborn German House of Bourbon, Lawrenceburg, KY

3 bedrooms·2 baths
Lawrenceburg • Kentucky
5(28 reviews)

$706.20 USD total for 3 nights

Nov 1 – 4, 2026

Lake Star Acres at Dale Hollow Lake
Lake Star Acres at Dale Hollow Lake
Lake Star Acres at Dale Hollow Lake
Lake Star Acres at Dale Hollow Lake
Lake Star Acres at Dale Hollow Lake

Lake Star Acres at Dale Hollow Lake

4 bedrooms·2 baths
Burkesville • Kentucky
5(21 reviews)

$1,210.00 USD total for 4 nights

Sep 22 – 26, 2026

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

Climb On Inn ~APT 1- Explore Comfort & Nature -RRG image 1
Climb On Inn ~APT 1- Explore Comfort & Nature -RRG image 2
Climb On Inn ~APT 1- Explore Comfort & Nature -RRG image 3
Climb On Inn ~APT 1- Explore Comfort & Nature -RRG image 4
Climb On Inn ~APT 1- Explore Comfort & Nature -RRG image 5

Climb On Inn ~APT 1- Explore Comfort & Nature -RRG

0 bedrooms·1 bath
Pine Ridge • Kentucky
4.85(204 reviews)

$700.60 USD total for 3 nights

Sep 22 – 25, 2026

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

The Patterson House
Front porch for early morning coffee
Foyer with study center
Livingroom with gas fireplace
Mobile TV/Stereo station

Historic Foursquare - walk to Asbury campuses

4 bedrooms·2 baths
Wilmore • Kentucky

$1,451.50 USD total for 3 nights

Sep 22 – 25, 2026

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)
CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG image 1
CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG image 2
CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG image 3
CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG image 4
CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG image 5

CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG

0 bedrooms·1 bath
Pine Ridge • Kentucky
4.91(160 reviews)

$593.85 USD total for 3 nights

Sep 22 – 25, 2026

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

Breaking Records - Steps from Paristown Hall
Breaking Records - Steps from Paristown Hall
Breaking Records - Steps from Paristown Hall
Breaking Records - Steps from Paristown Hall
Breaking Records - Steps from Paristown Hall

Breaking Records - Steps from Paristown Hall

3 bedrooms·1 bath
Louisville • Kentucky
5(9 reviews)

$580.80 USD total for 3 nights

Sep 22 – 25, 2026

Clifton Cutie!
Clifton Cutie!
Clifton Cutie!
Clifton Cutie!
Clifton Cutie!

Clifton Cutie!

1 bedroom·1 bath
Louisville • Kentucky
5(3 reviews)

$3,600.00 USD $1,875.00 USD total for 30 nights

Dec 4, 2026 – Jan 3, 2027

Dining room
Tranquility Corner image 2
Sliding gate on front porch to contain small pets or little ones.
Upstairs loft area
Upstairs loft seating area

Tranquility Corner

3 bedrooms·1 bath
Ashland • Kentucky
5(2 reviews)

$595.00 USD total for 3 nights

Sep 22 – 25, 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

Living Room
Deck on back
Master bedroom w/ Desk and Office Chair
Kitchen
2 Futons in basement

The Third Monkey

3 bedrooms·2½ baths
Williamstown • Kentucky
5(1 review)

$640.00 USD total for 3 nights

Sep 25 – 28, 2026

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

Hideaway on the River
Captain trundle
Second floor - Wet bar/ Pirate ship/ Full sized pool table
Hideaway on the River
Hideaway on the River

Hideaway on the River

3 bedrooms·2½ baths
Prospect • Kentucky
4.5(4 reviews)

$1,276.13 USD total for 3 nights

Sep 28 – Oct 1, 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

Enjoy cozy nights with s’mores around the fire
Comfortable common area perfect for relaxing.
Watch your favorite movies together on the Ruku tv..
Fully stocked kitchen
Plenty of space to prepare your favorite meals.,

Mi-Rose Cottage -Sleeps 8 - Pets Welcome

4 bedrooms·3 baths
Burnside • Kentucky
5(70 reviews)

$598.90 USD total for 3 nights

Sep 22 – 25, 2026