A river with a bridge and a city skyline in the background.

Holiday Homes in Kentucky

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Kentucky holiday homes

A modern dining area with a marble table, black chairs, and a vase of flowers. There is a ceiling fan and recessed lighting.

1. Charming 2-bedroom house on our farm with beautiful sunsets

Charming 2-bedroom house on our farm with beautiful sunsets
Stamping Ground
10.0 out of 10, Exceptional, (24 reviews)
"Our family loved the property.It was clean, had everything we needed, nice decor, and our daughter loved the horses. Close to the Ark Encounter. Would definitely recommend!"
United States
Glenita S.
The price is AU$324
includes taxes & fees
18 Oct - 19 Oct
Charming 2-bedroom house on our farm with beautiful sunsets
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dining table set with white plates and glasses.

2. Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Cave City
9.2 out of 10, Wonderful, (55 reviews)
"Clean rooms, nice beds, a bit older but has character. Once I was able to get in contact with owners communication was seamless. Easy check in and out. Super close to the caves which make this place worth it!"
United States
Justin
The price is AU$308
includes taxes & fees
18 Oct - 19 Oct
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
A spacious living area with a stone wall, wooden ceiling beams, a large chandelier, and a dining area with a stone countertop and bar stools.

3. 7 BR Lake Barkley Estate - Perfect for Family Gatherings, Reunions & Retreats

7 BR Lake Barkley Estate - Perfect for Family Gatherings, Reunions & Retreats
Cadiz
9.6 out of 10, Exceptional, (94 reviews)
"Large and well stocked home where our 3 families came together and enjoyed the lakeside getaway. The game room held many pool and tabletop shuffle board games. The kayaks and other lake toys were also enjoyed."
United States
Dave L.
7 BR Lake Barkley Estate - Perfect for Family Gatherings, Reunions & Retreats
A kitchen with wooden cabinets, a black refrigerator, and a coffee machine. There is a dining table with chairs and a chandelier.

4. "Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
Frankfort
9.8 out of 10, Exceptional, (203 reviews)
"Wonderful stay would recommend highly"
United States
Angie W.
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. Charming home in the heart of the city!

Charming home in the heart of the city!
Irish Hill
9.8 out of 10, Exceptional, (37 reviews)
"Great location, close to Bardstown Rd and hundreds of excellent restaurants. The back patio was a welcomed place to enjoy coffee in the mornings!!"
United States
Richard K.
Charming home in the heart of the city!
A modern living room with a brown leather sofa, a wooden floor, and a black spiral staircase.

6. Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!

Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!
Springfield
10.0 out of 10, Exceptional, (19 reviews)
"Absolutely adorable, great location, perfect for family, quiet, clean, great host, excellent communication!"
United States
Leanna C.
The price is AU$353
includes taxes & fees
20 Oct - 21 Oct
Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!
A kitchen with wooden cabinets, a dining area with a table and chairs, a chandelier, and a cross on the wall.

7. Country's Edge #2 Near the Ark Encounter!

Country's Edge #2 Near the Ark Encounter!
Berry
10.0 out of 10, Exceptional, (184 reviews)
"The property was very clean and our host was very helpful."
United States
Laura B.
Country's Edge #2 Near the Ark Encounter!
A modern kitchen with a wooden island, white cabinets, and a stainless steel refrigerator.

8. Magical Fairytale Stay in Nulu Historic District

Magical Fairytale Stay in Nulu Historic District
East Market District
9.4 out of 10, Exceptional, (18 reviews)
"Beautifully decorated and functional space. Close to NULU and convenient to everything."
United States
Mark L.
Magical Fairytale Stay in Nulu Historic District
A modern kitchen with granite countertops, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

9. Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.
Cave City
10.0 out of 10, Exceptional, (74 reviews)
"Great house and convenient to park. Lots of space to relax and was quiet."
United States
Theodore
The price is AU$248
includes taxes & fees
10 Nov - 11 Nov
Peaceful 2-bedroom home near Mammoth Cave.
A dining area with a wooden table, chairs, a piano, and a kitchen in the background.

10. Pet Friendly Small House in the Heart of Paducah

Pet Friendly Small House in the Heart of Paducah
Paducah
9.6 out of 10, Exceptional, (106 reviews)
"Great little house. Great decor! Close to some really great restaurant's and a fabulous park.....We (dogs included) really enjoyed our stay."
United States
Jennifer F.
The price is AU$327
includes taxes & fees
25 Oct - 26 Oct
Pet Friendly Small House in the Heart of Paducah
A modern living room with a sofa, coffee table, and dining area with chairs.

11. Bhie Lovely Hideaway | RRG | Peaceful | Cozy Stay. Stanton location, just steps from Kroger and a short 15-minute drive to Natural Bridge. Ideal home base for hikers + climbers, featuring a modern kitchen, firepit, grill, covered patio

Bhie Lovely Hideaway | RRG | Peaceful | Cozy Stay. Stanton location, just steps from Kroger and a short 15-minute drive to Natural Bridge. Ideal home base for hikers + climbers, featuring a modern kitchen, firepit, grill, covered patio
Stanton
9.8 out of 10, Exceptional, (29 reviews)
"The house was exactly as pictured. The beds were comfortable and the kitchen had plenty of space for cooking and hanging out. We had a great time exploring the gorge and would stay here again."
United States
Jason S.
Bhie Lovely Hideaway | RRG | Peaceful | Cozy Stay. Stanton location, just steps from Kroger and a short 15-minute drive to Natural Bridge. Ideal home base for hikers + climbers, featuring a modern kitchen, firepit, grill, covered patio
A swimming pool with lounge chairs, a hot tub, and a covered patio area.

12. 💙 BOURBON TRAIL on LAKE, HEATED POOL, GAME RM, PICKLEBALL, THEATRE, GOLF SIMULATOR!

💙 BOURBON TRAIL on LAKE, HEATED POOL, GAME RM, PICKLEBALL, THEATRE, GOLF SIMULATOR!
Lawrenceburg
10.0 out of 10, Exceptional, (12 reviews)
"Our Kentucky trip was absolutely beautiful! The home was exactly as described and made the perfect place for our family to relax and make unforgettable memories. We spent our days swimming, playing games, laughing, and simply enjoying every moment together. It was everything we hoped for and more. We would definitely stay here again!"
United States
Teresa V.
💙 BOURBON TRAIL on LAKE, HEATED POOL, GAME RM, PICKLEBALL, THEATRE, GOLF SIMULATOR!
A sunroom with a stone wall, large windows, a chandelier, and a sectional sofa.

13. Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Cherokee Seneca
10.0 out of 10, Exceptional, (164 reviews)
"Beautiful home and much grander than the pictures. Beds and accommodations were very comfortable. Our family from 79 to 7 would stay there again."
United States
Eileen S.
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
A covered patio with a piano, a hot tub, and outdoor furniture.

14. The Bunkhouse @Dragonfly Ranch is made to make you feel like home away from home

The Bunkhouse @Dragonfly Ranch is made to make you feel like home away from home
Cub Run
9.8 out of 10, Exceptional, (72 reviews)
"Dragonfly Ranch was a great landing spot after our time at Mammoth Cave. The house is well stocked with anything you might need, the country setting is peaceful, and the horses and dogs were a highlight for our kids."
United States
Steve V.
The price is AU$334
includes taxes & fees
20 Oct - 21 Oct
The Bunkhouse @Dragonfly Ranch is made to make you feel like home away from home
A living room with a fireplace, leather armchairs, a coffee table, and a painting on the wall.

15. New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
South Louisville
9.8 out of 10, Exceptional, (49 reviews)
"Great stay and great host"
United States
Chayil B.
The price is AU$322
includes taxes & fees
25 Oct - 26 Oct
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
A house with stone and siding exterior, a front porch, and potted plants.

16. Charming Highlands Carriage House 2 beds/2bath NO POOL

Charming Highlands Carriage House 2 beds/2bath NO POOL
Belknap
10.0 out of 10, Exceptional, (123 reviews)
"My son and I stayed here with our dog for four nights and it was exactly what we needed. The neighborhood is very nice and safe."
United States
Paul F.
Charming Highlands Carriage House 2 beds/2bath NO POOL
A modern living room with a sofa, coffee table, and a TV. A kitchen with appliances and a dining area is visible in the background.

17. The Caldwell - Germantown Highlands

The Caldwell - Germantown Highlands
Germantown
10.0 out of 10, Exceptional, (66 reviews)
"Amazing place to stay"
United States
Chris M.
The price is AU$326
includes taxes & fees
27 Oct - 28 Oct
The Caldwell - Germantown Highlands
A lakeside outdoor seating area with wooden chairs and a fire pit, surrounded by trees and a view of the lake.

18. Bourbon Trail River House

Bourbon Trail River House
Frankfort
9.6 out of 10, Exceptional, (61 reviews)
"The property was very nice and very clean. Would definitely stay again!"
United States
Gracelynn C.
Bourbon Trail River House
A house with a blue exterior, white trim, and a number 828 on the front.

19. The Chestnut - Nulu

The Chestnut - Nulu
Phoenix Hill
9.6 out of 10, Exceptional, (57 reviews)
"Great little property in a perfect location. We really enjoyed our stay."
United States
Creta B.
The price is AU$315
includes taxes & fees
28 Oct - 29 Oct
The Chestnut - Nulu
A covered deck with outdoor seating and a view of a lake.

20. Lakefront home near Mammoth Cave

Lakefront home near Mammoth Cave
Mammoth Cave
9.6 out of 10, Exceptional, (225 reviews)
"It was a good experience overall."
United States
Scott
Lakefront home near Mammoth Cave
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kentucky Hotel Reviews

Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

10/10 Excellent
"It was a little hard to find with all the one-way streets, but once we got there all went smooth. Also glad I paid up front for parking to be included!"
Terry 4-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Louisville Downtown by IHG

Find out more about Kentucky

Kentucky Holiday Homes information

Number of reviews
1,519
Accommodation
3328 Holiday Homes
Lowest Price
AU$248
Highest Price
AU$353

Explore a world of travel with Expedia