Top Vacation Homes in Kentucky in 2026

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Top Cities in Kentucky

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Louisville

A city skyline with illuminated buildings and a church spire.

Lexington

A cityscape with a mix of residential and commercial buildings, surrounded by greenery.

Bowling Green

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 building with a gravel driveway and a wooden deck leading to a set of double doors.

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 HK$932

HK$932

HK$1,745 total

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.

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

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

A living room with a sectional sofa, a glass coffee table, a patterned rug, a television, and a dark wooden cabinet.

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

The price is HK$699

HK$699

HK$1,694 total

includes taxes & fees

8 Oct - 9 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.

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

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

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

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

Cadiz

9.8 out of 10, Exceptional, (92 reviews)

9.8/10

Exceptional

(92 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, (194 reviews)

9.8/10

Exceptional

(194 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.

An outdoor patio with a rectangular table, four chairs, and a fire pit.

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

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, (35 reviews)

9.8/10

Exceptional

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

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

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 HK$882

HK$882

HK$1,877 total

includes taxes & fees

27 Sept - 28 Sept

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

A single-story house with a porch, a garage, and a tree in the foreground.

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, (182 reviews)

10/10

Exceptional

(182 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 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.

A room with a wooden floor, a patterned rug, a desk with a mirror, and a chair with a blanket.

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

8. Magical Fairytale Stay in Nulu Historic District

Magical Fairytale Stay in Nulu Historic District

East Market District

9.4 out of 10, Exceptional, (16 reviews)

9.4/10

Exceptional

(16 reviews)

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

Mark L.

The price is HK$776

HK$776

HK$2,349 total

includes taxes & fees

28 Sept - 29 Sept

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 single-story house with a dark blue exterior, a white front door, and a small porch.

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

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

9. Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.

Cave City

10.0 out of 10, Exceptional, (66 reviews)

10/10

Exceptional

(66 reviews)

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

Theodore

The price is HK$727

HK$727

HK$1,233 total

includes taxes & fees

29 Sept - 30 Sept

Peaceful 2-bedroom home near Mammoth Cave.

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

A single-story house with a front porch, a brick foundation, and a number '2046' on the door.

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

A modern kitchen with stainless steel appliances, dark cabinetry, and a patterned rug.

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 HK$988

HK$988

HK$1,744 total

includes taxes & fees

28 Sept - 29 Sept

Pet Friendly Small House in the Heart of Paducah

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

A hammock hanging from a tree in a park.

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.

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, wooden flooring, 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 covered patio with a piano, a hot tub, and outdoor furniture.

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

A bedroom with a canopy bed, a white door, and a window with a view of trees.

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

13. 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 price is HK$1,200

HK$1,200

HK$1,807 total

includes taxes & fees

6 Oct - 7 Oct

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

A sunroom with a stone wall, large windows, a chandelier, and a sectional sofa.

A dining area with a glass table and chairs, a potted plant, and a stone wall.

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

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

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

A white door with the number 2 and a 'WELCOME' sign above it.

15. 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 living room with a fireplace, leather armchairs, a coffee table, 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.

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

16. 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 HK$698

HK$698

HK$1,784 total

includes taxes & fees

25 Oct - 26 Oct

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

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 living room with a sofa, coffee table, and a sign on the wall.

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

17. The Caldwell - Germantown Highlands

The Caldwell - Germantown Highlands

Germantown

10.0 out of 10, Exceptional, (64 reviews)

10/10

Exceptional

(64 reviews)

"Amazing place to stay"

Chris M.

The price is HK$769

HK$769

HK$1,776 total

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 room with a large window overlooking a river, two chairs, a small table with a magazine, and a lamp.

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 wooden deck with a turquoise door and string lights.

A modern kitchen with wooden cabinets, granite countertops, a black refrigerator, and a built-in dishwasher.

19. The Chestnut - Nulu

The Chestnut - Nulu

Phoenix Hill

9.6 out of 10, Exceptional, (55 reviews)

9.6/10

Exceptional

(55 reviews)

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

Creta B.

The price is HK$699

HK$699

HK$1,676 total

includes taxes & fees

4 Oct - 5 Oct

The Chestnut - Nulu

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

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

A two-story building with a covered porch and a balcony.

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

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

10/10 Excellent

"Beautiful hotel and casino. Friendly staffy. Chad the barteneder was great. Restaurant was great (Olivers) Only complaint was the smells they are piping in are a little strong."

Maury 1-night trip

Posted 2 hours ago

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)