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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.

A grey sectional sofa with tufted detailing and multiple cushions.

A modern kitchen with white cabinets, a microwave, stove, and a ceiling fan.

A modern kitchen with white cabinets, a marble countertop, and a vase of dried flowers.

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, (23 reviews)

10/10

Exceptional

(23 reviews)

"Wonderful and responsive hosts! Such a beautiful and relaxing property! Will be back! "

Mary S.

The price is €205

€205

includes taxes & fees

12 Oct - 13 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.

A single-story house with a red roof, a front porch, and a small attached garage.

A house with a front porch, a decorative door, and a small garden area.

A neatly made bed with a wooden headboard, a rolled towel, and a white bedspread.

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

9.4 out of 10, Exceptional, (52 reviews)

9.4/10

Exceptional

(52 reviews)

"Perfect location for all the hiking trails and amazing coffee shop downtown!"

Ami

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.

A rustic interior with a stone wall, a fireplace, and a wooden ceiling.

A spacious interior with a stone wall, a wooden staircase, and a large chandelier.

A cozy living room with a stone wall, a large window, a wooden ceiling, and a fireplace.

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)

9.6/10

Exceptional

(94 reviews)

"This is a beautiful home with tons of room inside and out. When we weren’t outside, my family loved to hang out in the game room. The host was great to work with. I highly recommend this property for your next trip to Lake Barkley."

Ginger W.

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.

A bedroom with a wooden bed, a dresser, a rocking chair, and a ceiling fan.

A living room with two sofas, a coffee table, a fireplace, and a TV mounted on the wall.

A bar with a long counter displaying various glassware and bottles.

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, (197 reviews)

9.8/10

Exceptional

(197 reviews)

"Wonderful stay would recommend highly"

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.

A kitchen with a chessboard centerpiece, white cabinets, and a bar area.

A bedroom with a bed, a dark headboard, a window with curtains, and a framed picture on the wall.

A living room with a sofa, a coffee table, a bookshelf, and a door with windows.

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)

9.8/10

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!!"

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.

A room with a mirror, a wooden floor, a patterned rug, and a bed with a white headboard.

A modern building with a large garage door, a red door, and a covered porch area.

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, (18 reviews)

10/10

Exceptional

(18 reviews)

"Great location and the host was so wonderful! Will definitely stay again! "

Lucy W.

The price is €215

€215

includes taxes & fees

9 Oct - 10 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.

A bedroom with a tufted headboard, a patterned bedspread, a sliding barn door closet, and a small bedside table.

A modern kitchen with wooden cabinets, a black refrigerator, and a dining area with white chairs.

A covered wooden deck with a view of a green field and a white building in the distance.

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

Country's Edge #2 Near the Ark Encounter!

Berry

10.0 out of 10, Exceptional, (183 reviews)

10/10

Exceptional

(183 reviews)

"The property was very clean and our host was very helpful."

Laura B.

Country's Edge #2 Near the Ark Encounter!

A modern kitchen with a wooden island, white cabinets, and a stainless steel refrigerator.

A modern kitchen with white cabinets, stainless steel appliances, and blue LED strip lighting.

A dining area with a wooden table and benches, a brick wall with a 'TAVERN' sign, and a staircase leading to another room.

A living room with a dark grey sofa, a round white table, and a blue patterned ottoman. A wooden floor and a blue and white patterned rug are visible.

8. Magical Fairytale Stay in Nulu Historic District

Magical Fairytale Stay in Nulu Historic District

East Market District

9.4 out of 10, Exceptional, (17 reviews)

9.4/10

Exceptional

(17 reviews)

"Beautifully decorated and functional space. Close to NULU and convenient to everything."

Mark L.

The price is €271

€271

includes taxes & fees

4 Oct - 5 Oct

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.

A kitchen with white cabinets, a black stove, a microwave, a sink, and a coffee maker.

A modern kitchen with white cabinets, a central island with red chairs, and a dining area with a wooden table and chairs.

A bedroom with a wooden bed, two bedside tables, a nightstand, a wall-mounted light switch, and a painting of white flowers.

9. Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.

Cave City

10.0 out of 10, Exceptional, (71 reviews)

10/10

Exceptional

(71 reviews)

"Great house and convenient to park. Lots of space to relax and was quiet."

Theodore

Peaceful 2-bedroom home near Mammoth Cave.

A bedroom with a bed, nightstand, bench, dresser, and a mirror.

A dining area with a wooden table, chairs, a piano, and a kitchen in the background.

A hallway with wooden flooring, a chair, a table with a lamp, and a door leading to another room.

A living room with a sofa, coffee table, and bookshelves. There is a dining area in the background with a table and chairs.

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, (105 reviews)

9.6/10

Exceptional

(105 reviews)

"Great little house. Great decor! Close to some really great restaurant's and a fabulous park.....We (dogs included) really enjoyed our stay."

Jennifer F.

The price is €219

€219

includes taxes & fees

16 Oct - 17 Oct

Pet Friendly Small House in the Heart of Paducah

A modern living room with a sofa, coffee table, and dining area with chairs.

A living room with a sofa, a coffee table, a vase with flowers, a television, and a cabinet.

A modern kitchen with a marble countertop, built-in appliances, and a dining area with upholstered chairs.

A hammock hanging from a tree in a park.

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

10.0 out of 10, Exceptional, (27 reviews)

10/10

Exceptional

(27 reviews)

"It was perfect! Clean, cozy, private"

sue w.

A swimming pool with lounge chairs, a hot tub, and a covered patio area.

A large white house with a swimming pool, surrounded by a well-maintained lawn and a curved driveway.

A large house with a covered porch, multiple levels, and outdoor hot tubs.

A modern kitchen with a central island, bar stools, and pendant lighting.

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, (11 reviews)

10/10

Exceptional

(11 reviews)

"Our stay at Bourbon trails exceeded every expectation we had. From the moment we arrived, we were absolutely blown away. The property is even more breathtaking in person than the photos suggest, and every detail has clearly been designed with comfort, entertainment, and creating unforgettable memories in mind.There truly is something for everyone. The private heated pool was fantastic, the lake with the kayaks and paddleboards was beautiful and peaceful, and the illuminated fountain at night...

Frumie A.

💙 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.

A living room with a stone fireplace, leather armchair, and a glass coffee table.

A large, two-story stone house with a symmetrical facade, a central chimney, and a well-maintained lawn.

A rectangular swimming pool with a tiled deck, a covered patio area with outdoor furniture, and lush greenery in the background.

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, (159 reviews)

10/10

Exceptional

(159 reviews)

"Gorgeous well appointed home. Perfect for large group. Highly recommend!!"

Natalie L.

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.

A living room with a dining area, a fireplace, and a bookshelf.

A spacious room with a large brown leather sofa, a wooden bed, and a cowhide rug.

A white house with a porch, surrounded by a grassy field and trees.

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)

9.8/10

Exceptional

(72 reviews)

"The bunkhouse was incredibly clean and tidy, we all had an amazing stay and even ended up booking and extra night! The horses were fun to watch and next time we will definitely try and go out on a trail ride. Highly recommend, host was lovely and welcoming and we felt at home here so much so that it was really hard to leave!"

Misty F.

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.

A neatly made bed with a grey headboard, two bedside tables with lamps, and a painting on the wall.

A kitchen with a black stove, white cabinets, a glass table, and a chalkboard with a welcome message.

A living room with a sectional sofa, a coffee table, and artwork on the walls.

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, (47 reviews)

9.8/10

Exceptional

(47 reviews)

"Great stay and great host"

Chayil B.

The price is €210

€210

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.

A living room with a television on a white stand, a ceiling fan, a patterned armchair, and a window with curtains.

A living room with a television on a wooden stand, a patterned armchair, a sofa with a plaid blanket, and a decorative wall piece.

A staircase leading to a door with a window, carpeted steps, and a doormat.

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, (121 reviews)

10/10

Exceptional

(121 reviews)

"Great location! The place was very clean and the owners were very friendly. "

Kerry K.

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.

A modern kitchen with dark cabinetry, a stainless steel refrigerator, a central island with a butcher block, and pendant lighting.

A dining area with a table and chairs, a chandelier, a wall-mounted TV, and a window with blinds.

A two-story house with a front porch, a small front yard, and a visible staircase leading to the entrance.

17. The Caldwell - Germantown Highlands

The Caldwell - Germantown Highlands

Germantown

10.0 out of 10, Exceptional, (65 reviews)

10/10

Exceptional

(65 reviews)

"Amazing place to stay"

Chris M.

The price is €203

€203

includes taxes & fees

4 Oct - 5 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.

A garden with a stone fountain, various shrubs, and a wooden bench.

A living room with a sofa, ottoman, and armchair, a bookshelf, and a large window with a view.

A two-story house with a front porch, a garage, and a well-maintained lawn.

18. Bourbon Trail River House

Bourbon Trail River House

Frankfort

9.6 out of 10, Exceptional, (61 reviews)

9.6/10

Exceptional

(61 reviews)

"The property was very nice and very clean. Would definitely stay again!"

Gracelynn C.

Bourbon Trail River House

A house with a blue exterior, white trim, and a number 828 on the front.

A covered outdoor seating area with a sofa and two chairs, a small table, and a wooden deck.

A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a window with curtains.

A wooden deck with a turquoise door and string lights.

19. The Chestnut - Nulu

The Chestnut - Nulu

Phoenix Hill

9.6 out of 10, Exceptional, (56 reviews)

9.6/10

Exceptional

(56 reviews)

"Great little property in a perfect location. We really enjoyed our stay."

Creta B.

The price is €195

€195

includes taxes & fees

4 Oct - 5 Oct

The Chestnut - Nulu

A covered deck with outdoor seating and a view of a lake.

A spacious living area with a wooden dining table, grey sofas, and a ceiling fan.

A kitchen with wooden cabinets, stainless steel appliances, a central island with stools, and a window with blinds.

A bedroom with a bed, a ceiling fan, a nightstand, and a view of the outdoors.

20. Lakefront home near Mammoth Cave

Lakefront home near Mammoth Cave

Mammoth Cave

9.6 out of 10, Exceptional, (224 reviews)

9.6/10

Exceptional

(224 reviews)

"Beautiful location, fully stocked, and a lot of room for my family. I would love to stay there again!"

carol h.

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.

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Top Kentucky Hotel Reviews

Wingate by Wyndham Louisville Fair and Expo

8/10 Good

"Clean room great staff plenty parking. Your are by the highway but didn't bother us. Breakfast was good but was out of hot food both attempts we stayed 2 days ."

Christina 3-night trip

Posted 8 hours ago

Wingate by Wyndham Louisville Fair and Expo

Crowne Plaza Louisville Airport Expo Ctr by IHG

10/10 Excellent

"Excellent staff and service, Love having a restaurant in house, especially with none located nearby."

Patty 1-night trip

Posted 10 hours ago

Crowne Plaza Louisville Airport Expo Ctr by IHG

Cambria Hotel Louisville Downtown-Whiskey Row

10/10 Excellent

"Loved this hotel! Walking distance to everything you would want! The front office staff were friendly and courteous! We will definitely be back to stay!"

Karen 1-night trip

Posted 14 hours ago

Cambria Hotel Louisville Downtown-Whiskey Row

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent

"Clean hot l, breakfast was great and it is very accessible"

Anand 1-night trip

Posted 17 hours ago

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Louisville Downtown by IHG

10/10 Excellent

"No commo"

Ed 5-night trip

Posted 1 day ago

Holiday Inn Louisville Downtown by IHG

21c Museum Hotel Lexington

8/10 Good

"The restaurant wasn't ready so only room service was offered. They didn't honor my "breakfast included" stat. But, the property was centrally located for all visiting locations. And walkable to evening restaurants."

Carol 3-night trip

Posted 2 days ago

21c Museum Hotel Lexington

Radisson Hotel Cincinnati Riverfront

10/10 Excellent

"Paid for a city view this time, and it was definitely worth it!! This hotel always comes through!"

Katie 1-night trip

Posted 2 days ago

Radisson Hotel Cincinnati Riverfront

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Kentucky Holiday Homes information

Number of reviews	1,305
Accommodation	3305 Holiday Homes
Lowest Price	€195
Highest Price	€271

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Things to do in Lexington

Holiday Homes in Kentucky

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Kentucky holiday homes

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

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

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

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

5. Charming home in the heart of the city!

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

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

8. Magical Fairytale Stay in Nulu Historic District

9. Peaceful 2-bedroom home near Mammoth Cave.

10. Pet Friendly Small House in the Heart of Paducah

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

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

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

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

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

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

17. The Caldwell - Germantown Highlands

18. Bourbon Trail River House

19. The Chestnut - Nulu

20. Lakefront home near Mammoth Cave

Find holiday rentals that suit your style

Top Kentucky Hotel Reviews

Wingate by Wyndham Louisville Fair and Expo

Find out more about Kentucky

Kentucky Holiday Homes information

Explore a world of travel with Expedia