Owensboro Holiday Homes from £142: Search Holiday Homes in Owensboro

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

4 Oct - 5 Oct

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

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

Owensboro

Brad H.

includes taxes & fees

5 Oct - 6 Oct

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

3. 1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro

Johnny J.

includes taxes & fees

5 Oct - 6 Oct

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

4. Downtown Dream in Owensboro Ky

Owensboro

James K.

includes taxes & fees

21 Oct - 22 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.

5. Cozy Cottage home

Owensboro

falesha p.

includes taxes & fees

4 Oct - 5 Oct

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

6. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

Owensboro

John

includes taxes & fees

4 Oct - 5 Oct

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

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

Owensboro

includes taxes & fees

8 Oct - 9 Oct

A bedroom with a bed, two bedside tables, a ceiling fan, a neon sign, and a floral painting on the wall.

8. Cozy 2-bedroom house in Owensboro KY

Owensboro

BPCAT 0.

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

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

Owensboro

Jonathan M.

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a bed, nightstands, a ceiling fan, and a view into the dining area.

10. 3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown

Owensboro

includes taxes & fees

27 Oct - 28 Oct

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

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

Owensboro

Tyler C.

includes taxes & fees

14 Oct - 15 Oct

A kitchen with a stainless steel microwave, double sink, granite countertop, and a black oven.

12. Cozy Stylish 2 BR Home w / Relax & Enjoy

Owensboro

Carly J.

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

13. 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

28 Oct - 29 Oct

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

Owensboro

includes taxes & fees

4 Oct - 5 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

8 Oct - 9 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

2 Oct - 3 Oct

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

4 Oct - 5 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

Kristen J.

includes taxes & fees

8 Oct - 9 Oct

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

19. Trendy Two bedroom home centrally located near UE

Evansville

Scott D.

includes taxes & fees

4 Oct - 5 Oct

A modern living room with a white sofa, a black leather chair, a wooden coffee table, and a dining area in the background.

20. Abode à la Mode | Centrally Located 2BR/1BA Home / Fast wifi/Close to everything

Evansville

"We arrived around 8:30pm to find sleeping arrangements for 4 adults. The couch is about 4' long. We chose this place because it is listed as sleeping 5, but it's not. We woke up in the morning to shower and found a pitiful excuse of a shower. It dripped water. I took a video but unfortunately there is nowhere to upload it. It was sad. As if this wasn't enough, the kitchen utensils on the stove were covered in dried food and the vanity in the shower was not secure and fell off and landed on my...

Sam S.

includes taxes & fees

4 Oct - 5 Oct

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