Western Kentucky Holiday Houses

Western Kentucky Holiday Homes
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Our top choices for Western Kentucky holiday homes

A two-story building with a covered porch and a small staircase.

A brick house with a front porch, a star decoration, and a number '5183' on the door.

A kitchen with wooden cabinets, a white refrigerator, a microwave, a stove, and a coffee maker.

A living room with a dining table, sofas, a television, and a ceiling fan.

1. Nice and Quite place to stay

Nice and Quite place to stay

Madisonville

The price is NZ$646

NZ$646

includes taxes & fees

8 Oct - 9 Oct

Nice and Quite place to stay

An open-plan living area with a sofa, two armchairs, a ceiling fan, and a door leading to a balcony.

A living room with a dark door, two windows with blinds, a beige sofa, and a plant on a table.

A modern kitchen with dark cabinetry, a dining table with chairs, and a view through a glass door.

A living room with a brown leather sofa, a beige armchair, and a patterned ottoman. There are two windows with blinds, a door leading outside, and a floor lamp.

2. Loop Haven is an awesome place to stay.

Loop Haven is an awesome place to stay.

Madisonville

9.4 out of 10, Exceptional, (14 reviews)

9.4/10

Exceptional

(14 reviews)

"Nice clean space with room for everything we needed. Host was quick to always keep us up to date on our reservation, check in and check out.One minor issue was resolved immediately. Would stay here again although it's not fenced in on one side so luckily that was not an issue for us."

Dianne K.

The price is NZ$663

NZ$663

includes taxes & fees

8 Oct - 9 Oct

Loop Haven is an awesome place to stay.

A house with a porch, a large planter with red flowers, and a mailbox.

A round dining table with a white lace tablecloth, red and green plaid placemats, and red napkins with holly decorations. A red vase with a green plant is at the center.

A bedroom with a four-poster bed, a chandelier, wall-mounted lights, and a patterned rug.

A house entrance with two doors, a large potted plant, and a chandelier.

3. Guitars & Harmony

Guitars & Harmony

Central City

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

"Very nice decorations climate control was awesome. Great water pressure."

chuck

The price is NZ$553

NZ$553

includes taxes & fees

10 Oct - 11 Oct

Guitars & Harmony

A covered porch with a wooden floor, a bench, and a small Christmas tree.

A two-story house with a porch, a small front yard, and a mailbox.

A living room with a brown sofa, a white armchair, a coffee table, a piano, and a ceiling fan.

4. Bluegrass Bungalow 2 bedrooms with large porch

Bluegrass Bungalow 2 bedrooms with large porch

Owensboro

9.6 out of 10, Exceptional, (44 reviews)

9.6/10

Exceptional

(44 reviews)

"This was a great house in a perfect location for our stay in Owensboro. Really enjoyed our stay."

Jennifer A.

The price is NZ$329

NZ$329

includes taxes & fees

6 Oct - 7 Oct

Bluegrass Bungalow 2 bedrooms with large porch

A spacious dining area with a large wooden table and chairs, a kitchen with white cabinets, and a ceiling with wooden beams.

A bedroom with a bed, two bedside tables, a chandelier, and a window with blinds.

A living room with a sectional sofa, a wooden coffee table, a fireplace, and a chandelier.

A house with a porch featuring wicker furniture, a wooden door, and potted plants.

5. Littlefield Farmhouse in Princeton, KY

Littlefield Farmhouse in Princeton, KY

Princeton

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"Great stay! Would definitely go back"

Brandon K.

Littlefield Farmhouse in Princeton, KY

A living room with a fireplace, a ceiling fan, and a flat-screen TV.

A compact kitchen with wooden cabinets, a central island, and a dining area with chairs.

A single-story house with a front porch, a mailbox, and a number '907' on the door.

A kitchen with wooden cabinets, a countertop, a dishwasher, a toaster, and a sink.

6. Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

Owensboro

9.8 out of 10, Exceptional, (37 reviews)

9.8/10

Exceptional

(37 reviews)

"Very nice home with great amenities and owner was really great and helpful with any questions and needs."

Brad H.

The price is NZ$375

NZ$375

includes taxes & fees

11 Oct - 12 Oct

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

A modern kitchen with dark cabinets, a countertop, and a dining area with wooden chairs and a table.

A kitchen with a granite countertop, black sink, and dark cabinets.

A house with a front porch, a window with a white frame, and a small garden area with green shrubs.

7. 1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"We were in town for my daughter’s graduation, it was a 10 out of 10. We couldn’t have asked for a better place to stay. "

Johnny J.

The price is NZ$587

NZ$587

includes taxes & fees

19 Oct - 20 Oct

1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

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

A kitchen with a green textured wall, stainless steel sink, and black stove.

A bedroom with a bunk bed, a single bed, a ceiling fan, a round mirror, a nightstand, and a window with a view of the street.

A living room with a grey sofa, brown cushions, a neon sign on the wall, and a window.

8. Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat

Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat

Owensboro

The price is NZ$635

NZ$635

includes taxes & fees

11 Oct - 12 Oct

Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat

A two-story house with a red door, a small porch, and a well-maintained lawn.

A modern kitchen with white cabinetry, a stainless steel dishwasher, a built-in oven, and a microwave.

A neatly made bed with white bedding and two brown pillows, a bedside table with a lamp, and a blue curtain above the bed.

A neatly folded white towel on a white surface, a potted plant with green leaves, and a white vase.

9. 1520 Howard St B "HCB"

1520 Howard St B "HCB"

Evansville

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Nice place to stay, except for the traffic noise all night and the next door tenants that don't leave room for everyone to park."

scott c.

1520 Howard St B "HCB"

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A modern kitchen with a central island, bar stools, and a dining area with a table and chairs.

A white table with two cushioned benches, a decorative wall piece above, and a small vase with a plant.

A bedroom with a bed, a ceiling fan, a bedside table, a nightstand, a dresser, a chair, a window, and a mirror.

10. Charming 3-bedroom house with king bed , pet friendly

Charming 3-bedroom house with king bed , pet friendly

Owensboro

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Great location near food and groceries. Only 15 minutes from the convention center which was really nice for us. "

Tyler R.

The price is NZ$636

NZ$636

includes taxes & fees

7 Oct - 8 Oct

Charming 3-bedroom house with king bed , pet friendly

A two-story house with a front porch, a mailbox, and a street lamp.

A dining table with a glass top, surrounded by four chairs with cushioned seats. A blue vase with flowers is placed in the center.

A bedroom with a bed, a chair, a side table, a lamp, a ceiling fan, and a window with curtains.

A house with a patio area featuring a grill, outdoor furniture, and a decorative rug.

11. Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space

Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space

Greenville

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Awesome stay "

Gregory S.

The price is NZ$574

NZ$574

includes taxes & fees

6 Oct - 7 Oct

Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space

A modern living room with a sectional sofa, a coffee table, and decorative plants.

A bedroom with a bed, nightstands, a lamp, and a window.

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

A patio with two chairs and a small table, a white door, and a brick wall.

12. Trendy Two bedroom home centrally located near UE

Trendy Two bedroom home centrally located near UE

Evansville

9.0 out of 10, Wonderful, (11 reviews)

9.0/10

Wonderful

(11 reviews)

"Would stay again"

Scott D.

Trendy Two bedroom home centrally located near UE

A spacious kitchen with a central island, wooden cabinets, and a ceiling fan.

A single-story building with a metal roof, a front door, and two windows.

A small kitchenette with a coffee maker, mugs, and a tray of Folgers coffee.

A bedroom with a bed, a ceiling fan, an air conditioner, a nightstand, a lamp, and artwork on the walls.

13. Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

Elizabethtown

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Just a wonderful little cabin and extremely helpful host. Loved it"

Jeremiah 33:3 m.

The price is NZ$292

NZ$292

includes taxes & fees

6 Oct - 7 Oct

Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

A room with a wooden barn door, a dining area with blue chairs, and a washing machine in the background.

A building with a dark exterior, a wooden deck, and a sign reading "THE CLARK".

A compact kitchen with a red refrigerator, a washing machine, and a microwave. There is a blue table with two chairs and a star decoration on the wall.

A wooden staircase leading up to a deck, a blue folding chair, a small table, and a potted plant.

14. The Clark: Where Superheroes Sleep!

The Clark: Where Superheroes Sleep!

Metropolis

9.8 out of 10, Exceptional, (17 reviews)

9.8/10

Exceptional

(17 reviews)

"Great place to stay in Metropolis"

Ashley T.

The price is NZ$273

NZ$273

includes taxes & fees

6 Oct - 7 Oct

The Clark: Where Superheroes Sleep!

A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

A living room with a fireplace, two sofas, a coffee table, and a rug.

A balcony with wicker furniture, a wooden table, and a patterned rug.

A kitchen with a central island, white cabinets, a stove, and a dishwasher. There is a dining area with a table and chairs.

15. Downtown Dream in Owensboro Ky

Downtown Dream in Owensboro Ky

Owensboro

9.4 out of 10, Exceptional, (24 reviews)

9.4/10

Exceptional

(24 reviews)

"Everything was great, perfect location downtown. "

James K.

The price is NZ$838

NZ$838

includes taxes & fees

14 Oct - 15 Oct

Downtown Dream in Owensboro Ky

A lakeside property with a covered deck and a grassy area.

A hotel room with a fireplace, a sofa, a television, and two beds.

A row of single-story cabins with balconies, surrounded by trees and grassy areas.

16. Superior Suite- Bungalow overlooking the River

Superior Suite- Bungalow overlooking the River

Stone Church Precinct

9.4 out of 10, Exceptional, (31 reviews)

9.4/10

Exceptional

(31 reviews)

"Always fun stay here,beds r newer finally,good rest."

Donna d.

The price is NZ$319

NZ$319

includes taxes & fees

6 Oct - 7 Oct

Superior Suite- Bungalow overlooking the River

A cozy living room with a pool table, comfortable seating, and a staircase.

A two-story house with a front porch, a brick entrance, and a small garden with various plants.

A patio with a table and chairs, surrounded by a wooden deck and a hedge.

A living room with a brown armchair, a wooden coffee table with antlers, a lamp, and a deer head mounted on the wall.

17. Great for Family Reunions, Hunting Lodge And Pet Friendly!

Great for Family Reunions, Hunting Lodge And Pet Friendly!

Crofton

9.8 out of 10, Exceptional, (128 reviews)

9.8/10

Exceptional

(128 reviews)

"We had a wonderful stay at this property! The home was exactly as described. The host was responsive, friendly, and made the entire process seamless from booking through checkout."

Delia G.

The price is NZ$1,115

NZ$1,115

includes taxes & fees

6 Oct - 7 Oct

Great for Family Reunions, Hunting Lodge And Pet Friendly!

A modern kitchen with a built-in microwave, stainless steel appliances, and a sink.

A house with a porch, a blue Adirondack chair, and a black door.

A bedroom with a large bed, a nightstand, a dresser, and a wall with a beach-themed sign and artwork.

A kitchen with a stove, a spice rack, and a 'Welcome' sign.

18. Charming Home just minutes from Interstate and Mall

Charming Home just minutes from Interstate and Mall

Kevil

10.0 out of 10, Exceptional, (26 reviews)

10/10

Exceptional

(26 reviews)

"Location was great. Beds were so comfortable, place was so clean and nice. Very cute place to stay. Would stay here again!"

Deannena H.

The price is NZ$368

NZ$368

includes taxes & fees

6 Oct - 7 Oct

Charming Home just minutes from Interstate and Mall

A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table with chairs, and a window with blinds.

A neatly made bed with a wooden frame, a bedside table with a lamp, and a wall-mounted decorative piece.

A living room with a beige sofa, a coffee table, a floor lamp, a ceiling fan, and a window with curtains.

A round dining table with a patterned tablecloth, four chairs, and a potted orchid plant.

19. Great Home; Close to Everywhere.

Great Home; Close to Everywhere.

Oak Grove

9.8 out of 10, Exceptional, (60 reviews)

9.8/10

Exceptional

(60 reviews)

"I was very satisfied with the house and especially lived the huge backyard. Great location!!!!"

Yolanda J.

The price is NZ$568

NZ$568

includes taxes & fees

7 Oct - 8 Oct

Great Home; Close to Everywhere.

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

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

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

A kitchen with wooden cabinets, a black refrigerator, and a coffee sign.

20. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

Owensboro

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Extremely well-maintained property stocked with everything you could need. Host was accessible and very helpful."

John

The price is NZ$616

NZ$616

includes taxes & fees

1 Nov - 2 Nov

4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

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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Western Kentucky Holiday Homes information

Number of reviews	401
Accommodation	565 Holiday Homes
Lowest Price	NZ$273
Highest Price	NZ$1,115

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Holiday Homes in Western Kentucky

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Western Kentucky holiday homes

1. Nice and Quite place to stay

2. Loop Haven is an awesome place to stay.

3. Guitars & Harmony

4. Bluegrass Bungalow 2 bedrooms with large porch

5. Littlefield Farmhouse in Princeton, KY

6. Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

7. 1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

8. Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat

9. 1520 Howard St B "HCB"

10. Charming 3-bedroom house with king bed , pet friendly

11. Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space

12. Trendy Two bedroom home centrally located near UE

13. Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

14. The Clark: Where Superheroes Sleep!

15. Downtown Dream in Owensboro Ky

16. Superior Suite- Bungalow overlooking the River

17. Great for Family Reunions, Hunting Lodge And Pet Friendly!

18. Charming Home just minutes from Interstate and Mall

19. Great Home; Close to Everywhere.

20. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

Find holiday rentals that suit your style

Top Western Kentucky Hotel Reviews

Drury Inn Paducah

Find out more about Western Kentucky

Western Kentucky Holiday Homes information

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