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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Western Kentucky vacation homes

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

1. 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)
"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."
United States
Dianne K.
Loop Haven is an awesome place to stay.
A covered porch with a wooden floor, a bench, and a small Christmas tree.

2. Bluegrass Bungalow 2 bedrooms with large porch

Bluegrass Bungalow 2 bedrooms with large porch
Owensboro
9.6 out of 10, Exceptional, (45 reviews)
"This was a great house in a perfect location for our stay in Owensboro. Really enjoyed our stay."
United States
Jennifer A.
The price is ￥16,064
￥27,610 total
includes taxes & fees
Nov 8 - Nov 9
Bluegrass Bungalow 2 bedrooms with large porch
A spacious living room with hardwood floors, a wooden coffee table, a sofa, and a chandelier.

3. Littlefield Farmhouse in Princeton, KY

Littlefield Farmhouse in Princeton, KY
Princeton
10.0 out of 10, Exceptional, (45 reviews)
"Wonderful place to stay!"
United States
Beverly W.
The price is ￥19,844
￥32,205 total
includes taxes & fees
Nov 20 - Nov 21
Littlefield Farmhouse in Princeton, KY
Exterior

4. Stylish Southern Stay for Music Lovers & Getaways!

Stylish Southern Stay for Music Lovers & Getaways!
Owensboro
The price is ￥15,875
￥51,847 total
includes taxes & fees
Nov 13 - Nov 14
Stylish Southern Stay for Music Lovers & Getaways!
A two-story house with a front porch, a mailbox, and a street lamp.

5. 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)
"Awesome stay "
United States
Gregory S.
The price is ￥28,348
￥50,962 total
includes taxes & fees
Nov 7 - Nov 8
Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space
A living room with a fireplace, a ceiling fan, and a flat-screen TV.

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)
"Very nice home with great amenities and owner was really great and helpful with any questions and needs."
United States
Brad H.
The price is ￥17,009
￥31,871 total
includes taxes & fees
Nov 9 - Nov 10
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A modern living room with a sofa, coffee table, and a dining table.

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

Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
Owensboro
The price is ￥18,426
￥54,294 total
includes taxes & fees
Nov 13 - Nov 14
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
A house with a porch, a large planter with red flowers, and a mailbox.

8. Guitars & Harmony

Guitars & Harmony
Central City
9.8 out of 10, Exceptional, (22 reviews)
"Very good communication"
United States
Di
The price is ￥28,191
￥52,041 total
includes taxes & fees
Nov 30 - Dec 1
Guitars & Harmony
A neatly made bed with a 'WELCOME' pillow, a bedside table with a lamp, a ceiling fan, and a 'STAY awhile' sign on the wall.

9. Cozy Cottage home

Cozy Cottage home
Owensboro
10.0 out of 10, Exceptional, (5 reviews)
"Cute little cottage! We were in town for my son’s tournament and it worked great for a short stay with me, my husband and our two sons. Host had great communication and hospitality. Will book again if travel brings us back to this area. "
United States
Kristen C.
The price is ￥16,300
￥35,859 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Cottage home
A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

10. 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)
"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. "
United States
Johnny J.
The price is ￥17,269
￥44,223 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
A two-story house with a red door, a small porch, and a well-maintained lawn.

11. 1520 Howard St B "HCB"

1520 Howard St B "HCB"
Evansville
10.0 out of 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."
United States
scott c.
The price is ￥13,210
￥26,058 total
includes taxes & fees
Nov 12 - Nov 13
1520 Howard St B "HCB"
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

12. Enjoy mama’s House in a quiet little area of Crofton ky

Enjoy mama’s House in a quiet little area of Crofton ky
Crofton
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because my son got married at Burdoc Farms Oct 17th, 2026. The house was so cute, very clean and about 10 minutes from the venue. Any messages I sent to Phyllis, she got back to me promptly. The only downside was we would get back so late from setting up/wedding that it was too chilly to enjoy the front/back porch and gaze at all the stars. It’s just over a 2 hr drive (from Louisville) so if I needed a quick weekend reset, this would be the perfect quiet place to unwind."
United States
Shawn F.
Enjoy mama’s House in a quiet little area of Crofton ky
A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

13. 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)
"Extremely well-maintained property stocked with everything you could need. Host was accessible and very helpful."
United States
John
The price is ￥22,836
￥50,033 total
includes taxes & fees
Nov 8 - Nov 9
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
A campfire surrounded by a stone fire pit, with a dock extending into a calm lake.

14. Our home on Lake Malone is the perfect getaway. We call it "The Maya II"!

Our home on Lake Malone is the perfect getaway. We call it "The Maya II"!
Lewisburg
9.8 out of 10, Exceptional, (82 reviews)
"Nice place on the water. We really enjoyed being able to dock our boat. The only issue we had was no parking for a boat trailer."
United States
Andrew W.
The price is ￥29,766
￥57,294 total
includes taxes & fees
Nov 7 - Nov 8
Our home on Lake Malone is the perfect getaway. We call it "The Maya II"!
A cozy living room with a pool table, comfortable seating, and a staircase.

15. 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, (130 reviews)
"Great place with a lot of room. My youth group especially enjoyed the games downstairs"
United States
Andrew D.
The price is ￥59,059
￥108,155 total
includes taxes & fees
Nov 28 - Nov 29
Great for Family Reunions, Hunting Lodge And Pet Friendly!
A living room with blue walls, a ceiling fan, a large clock, a massage chair, a massage table, and a patterned rug.

16. Welcome to simple comfort a like new family friendly home Full of accommodation

Welcome to simple comfort a like new family friendly home Full of accommodation
Owensboro
10.0 out of 10, Exceptional, (22 reviews)
"Great location and the host was easy to communicate with."
United States
Jonathan M.
The price is ￥30,164
￥38,273 total
includes taxes & fees
Nov 8 - Nov 9
Welcome to simple comfort a like new family friendly home Full of accommodation
A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

17. Downtown Dream in Owensboro Ky

Downtown Dream in Owensboro Ky
Owensboro
9.4 out of 10, Exceptional, (26 reviews)
"Everything was great, perfect location downtown. "
United States
James K.
The price is ￥15,138
￥65,155 total
includes taxes & fees
Nov 16 - Nov 17
Downtown Dream in Owensboro Ky
A modern kitchen with white cabinets, a wooden island, and a gray sofa with yellow pillows.

18. Lake Country House on City Square

Lake Country House on City Square
Princeton
9.8 out of 10, Exceptional, (30 reviews)
"Our stay was excellent and even better we were close to family so we didn't need to travel far after activities."
United States
Stacey S.
The price is ￥21,261
￥43,404 total
includes taxes & fees
Nov 8 - Nov 9
Lake Country House on City Square
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table with chairs, and a window with blinds.

19. Great Home; Close to Everywhere.

Great Home; Close to Everywhere.
Oak Grove
9.8 out of 10, Exceptional, (60 reviews)
"Great property and owner. Would rent again."
United States
James J.
The price is ￥15,434
￥47,693 total
includes taxes & fees
Nov 8 - Nov 9
Great Home; Close to Everywhere.
A dining area with a dark wooden table, black chairs, a chandelier, and a cabinet with glass doors.

20. Becky's Place, Hopkinsville!

Becky's Place, Hopkinsville!
Hopkinsville
9.6 out of 10, Exceptional, (8 reviews)
"Amazing place to stay!!"
United States
Shauna K.
The price is ￥48,027
￥89,387 total
includes taxes & fees
Nov 10 - Nov 11
Becky's Place, Hopkinsville!
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 Western Kentucky Hotel Reviews

Harrah's Metropolis Hotel & Casino - A Caesars Rewards Destination

Harrah's Metropolis Hotel & Casino - A Caesars Rewards Destination

10/10 Excellent
"Great!"
Kimberly 3-night trip
Posted 1 hour ago
Harrah's Metropolis Hotel & Casino - A Caesars Rewards Destination

Find out more about Western Kentucky

Western Kentucky Vacation Homes information

Number of reviews
388
Accommodation
566 Vacation Homes
Lowest Price
￥26,058
Highest Price
￥108,155

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