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Our top choices for Western Kentucky holiday homes
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."
Dianne K.
The price is AU$509
includes taxes & fees
8 Nov - 9 Nov
2. Bluegrass Bungalow 2 bedrooms with large porch
Bluegrass Bungalow 2 bedrooms with large porchOwensboro
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."
Jennifer A.
The price is AU$252
includes taxes & fees
8 Nov - 9 Nov
3. Littlefield Farmhouse in Princeton, KY
Littlefield Farmhouse in Princeton, KYPrinceton
10.0 out of 10, Exceptional, (45 reviews)
"Wonderful place to stay!"
Beverly W.
The price is AU$317
includes taxes & fees
20 Nov - 21 Nov
4. Stylish Southern Stay for Music Lovers & Getaways!
Stylish Southern Stay for Music Lovers & Getaways!Owensboro
The price is AU$466
includes taxes & fees
12 Nov - 13 Nov
5. Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space
Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor spaceGreenville
10.0 out of 10, Exceptional, (10 reviews)
"Awesome stay "
Gregory S.
The price is AU$458
includes taxes & fees
9 Nov - 10 Nov
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."
Brad H.
The price is AU$276
includes taxes & fees
7 Nov - 8 Nov
7. Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR RetreatOwensboro
The price is AU$474
includes taxes & fees
19 Nov - 20 Nov
8. Guitars & Harmony
Guitars & HarmonyCentral City
9.8 out of 10, Exceptional, (22 reviews)
"Very good communication"
Di
The price is AU$464
includes taxes & fees
30 Nov - 1 Dec
9. Cozy Cottage home
Cozy Cottage homeOwensboro
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. "
Kristen C.
The price is AU$329
includes taxes & fees
19 Nov - 20 Nov
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 + PatioOwensboro
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. "
Johnny J.
The price is AU$402
includes taxes & fees
8 Nov - 9 Nov
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."
scott c.
The price is AU$229
includes taxes & fees
9 Nov - 10 Nov
12. Enjoy mama’s House in a quiet little area of Crofton ky
Enjoy mama’s House in a quiet little area of Crofton kyCrofton
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."
Shawn F.
The price is AU$668
includes taxes & fees
30 Nov - 1 Dec
13. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday WorldOwensboro
10.0 out of 10, Exceptional, (43 reviews)
"Extremely well-maintained property stocked with everything you could need. Host was accessible and very helpful."
John
The price is AU$455
includes taxes & fees
8 Nov - 9 Nov
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."
Andrew W.
The price is AU$509
includes taxes & fees
7 Nov - 8 Nov
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"
Andrew D.
The price is AU$958
includes taxes & fees
28 Nov - 29 Nov
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 accommodationOwensboro
10.0 out of 10, Exceptional, (22 reviews)
"Great location and the host was easy to communicate with."
Jonathan M.
The price is AU$349
includes taxes & fees
8 Nov - 9 Nov
17. Downtown Dream in Owensboro Ky
Downtown Dream in Owensboro KyOwensboro
9.4 out of 10, Exceptional, (26 reviews)
"Everything was great, perfect location downtown. "
James K.
The price is AU$649
includes taxes & fees
16 Nov - 17 Nov
18. Lake Country House on City Square
Lake Country House on City SquarePrinceton
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."
Stacey S.
The price is AU$388
includes taxes & fees
8 Nov - 9 Nov
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."
James J.
The price is AU$430
includes taxes & fees
8 Nov - 9 Nov
20. Becky's Place, Hopkinsville!
Becky's Place, Hopkinsville!Hopkinsville
9.6 out of 10, Exceptional, (8 reviews)
"Amazing place to stay!!"
Shauna K.
The price is AU$854
includes taxes & fees
8 Nov - 9 Nov
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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Tap your toes to the rhythms of musical Western Kentucky, a region with a rich character, historic communities and atmospheric natural beauty.
Photo by Dan Rose
Open Photo by Dan Rose