A building with a sign reading "1906 BEESOI" surrounded by blooming trees.

Rockport Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Rockport holiday rentals

A clear view of a swimming pool with a stone-lined edge and a wooden deck area in the background.

1. MILSuite separate entry...close to all things Owensboro and Daviess County.

MILSuite separate entry...close to all things Owensboro and Daviess County.
Owensboro
9.8 out of 10, Exceptional, (23 reviews)
"Second time staying at this location, both times have been exactly what I needed while in Owensboro. Attentive host and clean and tidy location equals a great and reasonably priced stay. Highly recommend for single travelers or couples looking for a place in Owensboro!"
United States
Randy W.
The price is HK$737
HK$1,281 total
includes taxes & fees
13 Oct - 14 Oct
MILSuite separate entry...close to all things Owensboro and Daviess County.
A modern kitchen with a TV, bar stools, and a trash can.

2. 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 HK$1,405
HK$2,047 total
includes taxes & fees
28 Sept - 29 Sept
The Blue Herron of Carpenters Lake
A bedroom with a bed, two bedside tables, a ceiling fan, a neon sign, and a floral painting on the wall.

3. Cozy 2-bedroom house in Owensboro KY

Cozy 2-bedroom house in Owensboro KY
Owensboro
10.0 out of 10, Exceptional, (2 reviews)
"Great stay great host"
United States
BPCAT 0.
The price is HK$1,020
HK$1,557 total
includes taxes & fees
27 Sept - 28 Sept
Cozy 2-bedroom house in Owensboro KY
A covered porch with a wooden floor, a bench, and a small Christmas tree.

4. 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$800
HK$1,449 total
includes taxes & fees
28 Sept - 29 Sept
Bluegrass Bungalow 2 bedrooms with large porch
A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

5. 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$779
HK$3,467 total
includes taxes & fees
29 Sept - 30 Sept
Downtown Dream in Owensboro Ky
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 HK$918
HK$2,805 total
includes taxes & fees
9 Oct - 10 Oct
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

7. 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 HK$860
HK$2,396 total
includes taxes & fees
27 Sept - 28 Sept
1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Charming 3-bedroom house with king bed , pet friendly
Owensboro
9.8 out of 10, Exceptional, (11 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$953
HK$2,828 total
includes taxes & fees
28 Sept - 29 Sept
Charming 3-bedroom house with king bed , pet friendly
A living room with a fireplace, a ceiling fan, and a flat-screen TV.

9. 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, (36 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$1,559 total
includes taxes & fees
28 Sept - 29 Sept
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
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.

10. 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 HK$812
HK$1,804 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Cottage home
A kitchen with a stainless steel microwave, double sink, granite countertop, and a black oven.

11. 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$953
HK$2,878 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Stylish 2 BR Home w / Relax & Enjoy
A living room with blue walls, a ceiling fan, a large clock, a massage chair, a massage table, and a patterned rug.

12. 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 HK$1,502
HK$1,998 total
includes taxes & fees
4 Oct - 5 Oct
Welcome to simple comfort a like new family friendly home Full of accommodation
A bedroom with a bed, nightstands, a ceiling fan, and a view into the dining area.

13. 3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown

3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
Owensboro
The price is HK$882
HK$2,441 total
includes taxes & fees
4 Oct - 5 Oct
3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
A modern kitchen with a black refrigerator, white cabinets, and a marble dining table with chairs.

14. 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$1,045
HK$3,066 total
includes taxes & fees
4 Oct - 5 Oct
Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
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, (119 reviews)
"Awesome place to have some time with family away from everyone."
United States
Lori
The price is HK$776
HK$1,192 total
includes taxes & fees
1 Oct - 2 Oct
Charming Treehouse with Lake View and Access
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

16. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
The price is HK$1,176
HK$3,091 total
includes taxes & fees
28 Sept - 29 Sept
The Cowboys Slumber' 2 Mi to Lincoln State Park
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

17. 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 HK$699
HK$2,280 total
includes taxes & fees
4 Oct - 5 Oct
The Bluegrass Barbie
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

18. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (1 review)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
The price is HK$863
HK$3,171 total
includes taxes & fees
29 Sept - 30 Sept
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden interior with a television, wooden cabinets, and a plant.

19. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (73 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is HK$1,121
HK$1,432 total
includes taxes & fees
30 Sept - 1 Oct
Guest House with acreage to explore.
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, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is HK$1,014
HK$3,217 total
includes taxes & fees
30 Sept - 1 Oct
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.
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Top Rockport Hotel Reviews

DoubleTree by Hilton Evansville

DoubleTree by Hilton Evansville

10/10 Excellent
"n/a"
Austin 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Evansville

Find out more about Rockport

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

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

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

Frequently asked questions

Are there holiday rentals in Rockport?

Yes, there are holiday rentals close to the most popular sights in Rockport, or you can select a more secluded option if you're looking for a relaxing stay. Rockport is known for its shopping and riverfront.

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

Oakside Retreat – Private Getaway with Huge Yard, Firepit and Game Room: This holiday home rental outside of Rockport offers a selection of games, a BBQ and air conditioning 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.

What can I see and do in Rockport?

While exploring the area, visit family-friendly sights like International Bluegrass Music Museum, or get outside and enjoy nature at Ohio River Valley. In the wider area, you’ll find Lincoln Pioneer Village and Museum and Kentucky Wesleyan College.

What are holiday rentals like in Rockport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rockport. Holiday rentals offer amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family trip.