Owensboro Holiday Homes from €169: Search Top House Rentals

A large, rusted steel bridge over a river, surrounded by a park with trees and a playground.

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Our top choices for Owensboro holiday homes

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

1. Bluegrass Bungalow 2 bedrooms with large porch

Owensboro

Jennifer A.

includes taxes & fees

22 Oct - 23 Oct

2. Stylish Southern Stay for Music Lovers & Getaways!

Owensboro

includes taxes & fees

28 Oct - 29 Oct

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

3. Downtown Dream in Owensboro Ky

Owensboro

James K.

includes taxes & fees

26 Oct - 27 Oct

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

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

Owensboro

Brad H.

includes taxes & fees

25 Oct - 26 Oct

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

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

Owensboro

includes taxes & fees

28 Oct - 29 Oct

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.

6. Cozy Cottage home

Owensboro

falesha p.

includes taxes & fees

1 Nov - 2 Nov

A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

7. The Bluegrass Barbie

Owensboro

"After staying for several weeks, we can say with confidence that our host, Kelsey, and the Bluegrass Barbie house exceeded our expectations! Kelsey was so friendly and made our experience an easy one. She was accessible to us, very responsive, and accommodating throughout our stay. She made the process seamless. The home has great curb appeal and is located in a nice neighborhood where we felt very safe. We felt welcomed when we walked in the door. Inside, the home was very clean throughout...

Jessica S.

includes taxes & fees

16 Nov - 17 Nov

A dining area with a table set for four, a ceiling fan, and a view into a bedroom.

8. 3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown

Owensboro

Isaac D.

includes taxes & fees

8 Nov - 9 Nov

A laundry room with a washing machine, dryer, and stacked laundry baskets.

9. 1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro

Johnny J.

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

10. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

Owensboro

John

includes taxes & fees

26 Oct - 27 Oct

A living room with blue walls, a ceiling fan, a large clock, a massage chair, a massage table, and a patterned rug.

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

Owensboro

Jonathan M.

includes taxes & fees

22 Oct - 23 Oct

A modern kitchen with a black refrigerator, white cabinets, and a marble dining table with chairs.

12. Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!

Owensboro

Tyler C.

includes taxes & fees

16 Nov - 17 Nov

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

13. Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB

Owensboro

includes taxes & fees

22 Oct - 23 Oct

A room with purple walls, a fireplace, a television, and a patterned rug.

14. The Regal - Spacious 4-Bedroom Historic Retreat

Owensboro

"Awesome property and very responsive owner.Great location and very safe and secure..House is very unique and eclectic and nicely decorated..Rooms are spacious and great beds( my favorite was downstairs master)Host has everything you could possibly need for your stay whether it be long or short..We had issue w cooling and was able to contact host and they were there almost immediately to remedy the situation.Only draw back to our stay was there is no washer or dryer...We had a large group and...

includes taxes & fees

22 Oct - 23 Oct

A bedroom with a wooden ladder, a dresser, a wall-mounted TV, and a window with blinds.

15. Get ready for a Spellbinding Themed Getaway at Owensboro!

Owensboro

"About 10 minutes after our 3 pm check in time I used the provide codes to enter the property. Once inside I found a man who had been staying there a couple of days saying there was a mistake. We both tried calling the host and got an answering machine. I made the reservation over a month ago. I left and checked my email. I had an email a little before 1 saying my reservation was canceled and a refund issued. After seeing the place and the area I would not have felt comfortable staying there. It...

Barbara B.

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a TV, bar stools, and a trash can.

16. The Blue Herron of Carpenters Lake

Maceo

Stephanie A.

includes taxes & fees

21 Nov - 22 Nov

A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

17. Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

Newburgh

Julia F.

includes taxes & fees

27 Oct - 28 Oct

A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

18. Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Newburgh

chris g.

includes taxes & fees

20 Nov - 21 Nov

A stone fireplace with a Christmas tree and decorations, a white sofa, and a window with a view.

19. Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path

Lewisport

Favour R.

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

20. Trendy Two bedroom home centrally located near UE

Evansville

Scott D.

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Top Owensboro Hotel Reviews

Greenfield Inn & Suites Owensboro, KY Airport

10/10 Excellent

"Stayed many times and always is a pleasant experience."

Hampton Inn Owensboro South

10/10 Excellent

"I can not say enough about the kindness of the staff! Wow! Not just check in but throughout our staff and 90% that we passed in the hallways! Incredible people! Hotel a little noisy first thing but nothing that would make me think twice - just different schedules. I would definitely recommend! Pool was closed for the season so that was the only downside but we have come to realize that was some with all the pools on our trip and it mentions right on website if you read! Thank you !!!"

Find out more about Owensboro

Owensboro Holiday Homes information

Number of reviews	275
Accommodation	126 Holiday Homes
Lowest Price	€169
Highest Price	€604

Room 1

Change your mind

Treat yourself

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Check prices for these dates

Our top choices for Owensboro holiday homes

1. Bluegrass Bungalow 2 bedrooms with large porch