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

Holiday Homes in Owensboro

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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

Bluegrass Bungalow 2 bedrooms with large porch
Owensboro
9.6 out of 10, Exceptional, (44 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 NZ$329
includes taxes & fees
18 Oct - 19 Oct
Bluegrass Bungalow 2 bedrooms with large porch
A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

2. Downtown Dream in Owensboro Ky

Downtown Dream in Owensboro Ky
Owensboro
9.4 out of 10, Exceptional, (24 reviews)
"Everything was great, perfect location downtown. "
United States
James K.
The price is NZ$883
includes taxes & fees
5 Nov - 6 Nov
Downtown Dream in Owensboro Ky
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

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 NZ$537
includes taxes & fees
19 Oct - 20 Oct
1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
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!

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 NZ$373
includes taxes & fees
18 Oct - 19 Oct
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A bedroom with a bed, nightstands, a ceiling fan, and a view into the dining area.

5. 3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown

3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
Owensboro
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful time here. The home was easy to check in to and the host was very responsive."
United States
Isaac D.
The price is NZ$539
includes taxes & fees
25 Oct - 26 Oct
3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
A modern living room with a sofa, coffee table, and a dining table.

6. 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$628
includes taxes & fees
24 Oct - 25 Oct
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
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.

7. Cozy Cottage home

Cozy Cottage home
Owensboro
10.0 out of 10, Exceptional, (4 reviews)
"Was very nice clean and host was great"
United States
falesha p.
The price is NZ$440
includes taxes & fees
15 Nov - 16 Nov
Cozy Cottage home
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

8. The Bluegrass Barbie

The Bluegrass Barbie
Owensboro
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Jessica S.
The price is NZ$519
includes taxes & fees
28 Oct - 29 Oct
The Bluegrass Barbie
A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

9. 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 NZ$603
includes taxes & fees
26 Oct - 27 Oct
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
A living room with blue walls, a ceiling fan, a large clock, a massage chair, a massage table, and a patterned rug.

10. 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 NZ$451
includes taxes & fees
20 Oct - 21 Oct
Welcome to simple comfort a like new family friendly home Full of accommodation
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!

Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
Owensboro
6.0 out of 10, (2 reviews)
"The home was very clean and the host was quick to answer any questions I had. My daughter had a volleyball tournament in Owensboro and the house was cheaper than a hotel! I will forever be thankful that the Lord placed this home on my options. It was beautiful and a great place to stay! 1000/10 recommend."
United States
Tyler C.
Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
Private kitchen

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

Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB
Owensboro
The price is NZ$1,143
includes taxes & fees
22 Oct - 23 Oct
Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB
A bedroom with a wooden ladder, a dresser, a wall-mounted TV, and a window with blinds.

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

Get ready for a Spellbinding Themed Getaway at Owensboro!
Owensboro
2.0 out of 10, (1 review)
The price is NZ$610
includes taxes & fees
28 Oct - 29 Oct
Get ready for a Spellbinding Themed Getaway at Owensboro!
A room with purple walls, a fireplace, a television, and a patterned rug.

14. The Regal - Spacious 4-Bedroom Historic Retreat

The Regal - Spacious 4-Bedroom Historic Retreat
Owensboro
10.0 out of 10, Exceptional, (1 review)
"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...
United States
D
The price is NZ$1,539
includes taxes & fees
22 Oct - 23 Oct
The Regal - Spacious 4-Bedroom Historic Retreat
A modern kitchen with a TV, bar stools, and a trash can.

15. The Blue Herron of Carpenters Lake

The Blue Herron of Carpenters Lake
Maceo
8.4 out of 10, Very good, (5 reviews)
"Very clean, they had everything you could possibly need to start, the complementary items was a nice gesture, love my cup of coffee looking at the lake, my kids love it they didn't want to leave, very beautiful home for a weekend getaway recommended 100% we enjoyed our stay."
United States
Stephanie A.
The price is NZ$460
includes taxes & fees
19 Oct - 20 Oct
The Blue Herron of Carpenters Lake
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

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

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is NZ$671
includes taxes & fees
19 Oct - 20 Oct
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

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

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.6 out of 10, Exceptional, (45 reviews)
"Great location, quiet but still close to shopping and restaurants. Use of the garage was a plus as it was raining the day we were packing up to leave."
United States
chris g.
The price is NZ$520
includes taxes & fees
22 Oct - 23 Oct
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A stone fireplace with a Christmas tree and decorations, a white sofa, and a window with a view.

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

Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
Lewisport
10.0 out of 10, Exceptional, (2 reviews)
"What a great place to stay to get away from it all with the family! "
United States
Favour R.
The price is NZ$551
includes taxes & fees
19 Oct - 20 Oct
Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
A modern living room with a sectional sofa, a coffee table, and decorative plants.

19. 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)
"Would stay again"
United States
Scott D.
The price is NZ$345
includes taxes & fees
19 Oct - 20 Oct
Trendy Two bedroom home centrally located near UE
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

20. Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.

Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
Evanston
10.0 out of 10, Exceptional, (29 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
The price is NZ$580
includes taxes & fees
19 Oct - 20 Oct
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
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 Owensboro Hotel Reviews

Hampton Inn & Suites Downtown Owensboro/Waterfront

Hampton Inn & Suites Downtown Owensboro/Waterfront

10/10 Excellent
"Gf"
Kimala 2-night trip
Posted 3 hours ago
Hampton Inn & Suites Downtown Owensboro/Waterfront

Find out more about Owensboro

Owensboro Holiday Homes information

Number of reviews
302
Accommodation
106 Holiday Homes
Lowest Price
NZ$329
Highest Price
NZ$1,143