Location

Dates

Guests

Vacation rentals in Kentucky

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)

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

Quiet, remodeled home near I-24

Quiet, remodeled home near I-24

Quiet, remodeled home near I-24

Quiet, remodeled home near I-24

Quiet, remodeled home near I-24

Quiet, remodeled home near I-24

3 bedrooms·1 bath

Paducah • Kentucky

5(8 reviews)

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)

8448 Hempridge

4 bedrooms·2½ baths

Shelbyville • Kentucky

Airport CVG 2 Queen Room | Breakfast, Pool & Gym image 1

Airport CVG 2 Queen Room | Breakfast, Pool & Gym image 2

Airport CVG 2 Queen Room | Breakfast, Pool & Gym image 3

Airport CVG 2 Queen Room | Breakfast, Pool & Gym image 4

Airport CVG 2 Queen Room | Breakfast, Pool & Gym image 5

Airport CVG 2 Queen Room | Breakfast, Pool & Gym

1 bedroom·1 bath

Hebron • Kentucky

$335.96 USD total for 3 nights

Sep 22 – 25, 2026

Airport CVG King Room | Breakfast, Pool & Gym image 1

Airport CVG King Room | Breakfast, Pool & Gym image 2

Airport CVG King Room | Breakfast, Pool & Gym image 3

Airport CVG King Room | Breakfast, Pool & Gym image 4

Airport CVG King Room | Breakfast, Pool & Gym image 5

Airport CVG King Room | Breakfast, Pool & Gym

1 bedroom·1 bath

Hebron • Kentucky

$306.74 USD total for 3 nights

Sep 22 – 25, 2026

Marc’s Museum

7 bedrooms·2½ baths

Kuttawa • Kentucky

$200 – $225/ night(excl. fees & taxes)

Marcaritaville

4 bedrooms·2 baths

Kuttawa • Kentucky

$886.00 USD total for 3 nights

Jan 1 – 4, 2027

Street view of property

Outdoor gas grill

Den with desk work space

Full kitchen stocked for cooking and entertaining

The Luxurious Lustron House

4 bedrooms·2 baths

Barbourville • Kentucky

5(59 reviews)

$298 – $400/ night(excl. fees & taxes)

Steps to the creek

Private kitchen

Bedroom 2 (king bed)

Creek-Front Getaway at Dale Hollow Lake

3 bedrooms·2 baths

Albany • Kentucky

5(5 reviews)

$1,547.28 USD total for 3 nights

Oct 4 – 7, 2026

Street view of property

Juliet’s Place

5 bedrooms·3 baths

Barbourville • Kentucky

5(4 reviews)

$298 – $400/ night(excl. fees & taxes)

Charming Lakefront 4br/3ba Estate on Rough River!

Charming Lakefront 4br/3ba Estate on Rough River!

Charming Lakefront 4br/3ba Estate on Rough River!

Charming Lakefront 4br/3ba Estate on Rough River!

Charming Lakefront 4br/3ba Estate on Rough River!

Charming Lakefront 4br/3ba Estate on Rough River!

4 bedrooms·1 bath

McDaniels • Kentucky

5(2 reviews)

$901.00 USD total for 3 nights

Sep 22 – 25, 2026

Red roof bungalow in downtown Hot*Tub Bourbon TRL image 1

Space for three cars off street parking

Red roof bungalow in downtown Hot*Tub Bourbon TRL image 4

Outdoor dining with grill

Sunset from backyard does include the city cemetery but the neighbors are quiet indeed. Many locals use this cemetery for walking. You’ll see owls, rabbits and other wildlife.

Red roof bungalow in downtown Hot*Tub Bourbon TRL

2 bedrooms·1 bath

Versailles • Kentucky

4(2 reviews)

$4,650.00 USD total for 30 nights

Sep 22 – Oct 22, 2026

My Campaign image 1

My Campaign image 2

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My Campaign

2 bedrooms·1 bath

Lexington • Kentucky

5(2 reviews)

$447.00 USD total for 3 nights

Sep 29 – Oct 2, 2026