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

Owensboro Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Owensboro holiday rentals

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 HK$799
HK$1,448 total
includes taxes & fees
27 Aug - 28 Aug
Bluegrass Bungalow 2 bedrooms with large porch
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!

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
Owensboro
9.8 out of 10, Exceptional, (35 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 HK$776
HK$1,577 total
includes taxes & fees
27 Aug - 28 Aug
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

3. 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 HK$745
HK$3,602 total
includes taxes & fees
31 Aug - 1 Sept
Downtown Dream in Owensboro Ky
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.

4. Cozy Cottage home

Cozy Cottage home
Owensboro
10.0 out of 10, Exceptional, (3 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 HK$811
HK$1,886 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Cottage home

5. Cozy 2-bedroom house in Owensboro KY

Cozy 2-bedroom house in Owensboro KY
Owensboro
10.0 out of 10, Exceptional, (2 reviews)
"Clean house. Host very responsive. Property as described."
United States
David O.
The price is HK$1,019
HK$1,582 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 2-bedroom house in Owensboro KY
A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

6. 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, (23 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 HK$1,011
HK$2,554 total
includes taxes & fees
30 Aug - 31 Aug
1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

7. 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, (42 reviews)
"Was exactly what we were looking for! Very clean and they provided everything we could’ve possibly needed. Great communication as well! Would definitely stay here in the future. "
United States
Joshua M.
The price is HK$1,089
HK$2,637 total
includes taxes & fees
31 Aug - 1 Sept
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
A modern living room with a sofa, coffee table, and a dining table.

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

Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
Owensboro
The price is HK$917
HK$2,858 total
includes taxes & fees
1 Sept - 2 Sept
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

9. Charming 3-bedroom house with king bed , pet friendly

Charming 3-bedroom house with king bed , pet friendly
Owensboro
9.6 out of 10, Exceptional, (10 reviews)
"Great location near food and groceries. Only 15 minutes from the convention center which was really nice for us. "
United States
Tyler R.
The price is HK$1,058
HK$3,006 total
includes taxes & fees
27 Aug - 28 Aug
Charming 3-bedroom house with king bed , pet friendly
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

10. The Bluegrass Barbie

The Bluegrass Barbie
Owensboro
The price is HK$698
HK$2,315 total
includes taxes & fees
8 Sept - 9 Sept
The Bluegrass Barbie
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
The price is HK$1,044
HK$3,238 total
includes taxes & fees
20 Sept - 21 Sept
Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
A kitchen with a stainless steel microwave, double sink, granite countertop, and a black oven.

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

Cozy Stylish 2 BR Home w / Relax & Enjoy
Owensboro
9.4 out of 10, Exceptional, (3 reviews)
"The host was easy to communicate with. The house was very clean, new appliances, spacious and comfortable. I highly recommend this property when staying in the Owensboro area"
United States
Carly J.
The price is HK$1,023
HK$3,000 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Stylish 2 BR Home w / Relax & Enjoy

13. THE PINK LIMOZEEN - Charming 3-bedroom house with pool in Owensboro

THE PINK LIMOZEEN - Charming 3-bedroom house with pool in Owensboro
Owensboro
The price is HK$1,834
HK$4,315 total
includes taxes & fees
8 Sept - 9 Sept
THE PINK LIMOZEEN - Charming 3-bedroom house with pool in Owensboro

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

Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB
Owensboro
The price is HK$2,233
HK$5,472 total
includes taxes & fees
1 Sept - 2 Sept
Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB
A wooden observation tower with a small deck and stairs, surrounded by trees.

15. Charming Treehouse with Lake View and Access

Charming Treehouse with Lake View and Access
Utica
9.8 out of 10, Exceptional, (115 reviews)
"We had a wonderful stay. Thank you for having such a beautiful place to enjoy. "
United States
Terah W.
The price is HK$776
HK$1,191 total
includes taxes & fees
27 Aug - 28 Aug
Charming Treehouse with Lake View and Access
A rustic cabin with a stone foundation, wooden siding, and a covered porch.

16. Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro

Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
Utica
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful spot! The best "
United States
Andrea S.
The price is HK$846
HK$2,100 total
includes taxes & fees
2 Sept - 3 Sept
Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
A modern kitchen with a TV, bar stools, and a trash can.

17. The Blue Herron of Carpenters Lake

The Blue Herron of Carpenters Lake
Maceo
8.0 out of 10, Very good, (4 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 HK$1,404
HK$2,072 total
includes taxes & fees
27 Aug - 28 Aug
The Blue Herron of Carpenters Lake
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.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.6 out of 10, Exceptional, (43 reviews)
"We have absolutely loved it here the wildlife the owners are amazing. I hope that next time we’re in town will be able to stay here again."
United States
Kristen J.
The price is HK$719
HK$2,175 total
includes taxes & fees
27 Aug - 28 Aug
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dishwasher. There's a small dining area with a table and chairs, and a red sofa in the living room.

19. RiverStone Retreat D

RiverStone Retreat D
Newburgh
9.0 out of 10, Wonderful, (2 reviews)
"Toilet moves when you sit on it, needs fixed!Good cooling and A/C!Need more towels ahead of time (face, hand and bath sizes) without having to ask after checking in. I listed 3 guests and did not have enough for 1 guest and the length of stay. Once should not have to request the minimum needed.Thank you for providing them once requested however!"
United States
jim a.
The price is HK$602
HK$1,306 total
includes taxes & fees
30 Aug - 31 Aug
RiverStone Retreat D
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

20. 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, (19 reviews)
"Enjoyed the stay immensely. Very clean. Will stay again. "
United States
Mary P.
The price is HK$946
HK$3,280 total
includes taxes & fees
8 Sept - 9 Sept
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Owensboro Hotel Reviews

Home2 Suites By Hilton Owensboro

Home2 Suites By Hilton Owensboro

8/10 Good
"Decent spot lots of construction around it"
Kameron 1-night trip
Posted 4 hours ago
Home2 Suites By Hilton Owensboro

Find out more about Owensboro

Search for holiday rentals in Owensboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Owensboro using one of the methods below:

  • View our selection of featured holiday rentals in Owensboro
  • Use the map to find apartments and other holiday homes in the Owensboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Owensboro while they last

Look no further and take a look at our great range of rental properties in Owensboro!

Frequently asked questions

Can I find holiday rentals in Owensboro?

Yes, there are holiday rentals in Owensboro close to International Bluegrass Music Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and riverfront in Owensboro. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Owensboro has to offer?

Blue Moon Cottage: Historic Owensboro Home w/ Large Pool, Music Room, Location!: This highly rated holiday home rental in Owensboro offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Some other homes for rent in Owensboro include Welcome to simple comfort a like new family friendly home Full of accommodation and Bluegrass Bungalow 2 bedrooms with large porch.

How many holiday rentals will I find in Owensboro?

Expedia has 47 holiday rentals for your stay in Owensboro.

What’s there to see and do in Owensboro?

Family-friendly attractions include International Bluegrass Music Museum and Owensboro Museum of Science and History, whereas Smothers Park and Riverfront Park are a couple of great spots to enjoy the outdoors. While here, Green River and Ohio River Valley are other places worth a visit.

What’s a holiday rental in Owensboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Owensboro. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.