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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Rockport holiday rentals

A living room with a TV, wooden coffee table, potted plant, and a vase of tulips.

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, (24 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 AU$228
includes taxes & fees
25 Oct - 26 Oct
MILSuite separate entry...close to all things Owensboro and Daviess County.
Exterior

2. Stylish Southern Stay for Music Lovers & Getaways!

Stylish Southern Stay for Music Lovers & Getaways!
Owensboro
The price is AU$490
includes taxes & fees
29 Oct - 30 Oct
Stylish Southern Stay for Music Lovers & Getaways!
A covered porch with a wooden floor, a bench, and a small Christmas tree.

3. Bluegrass Bungalow 2 bedrooms with large porch

Bluegrass Bungalow 2 bedrooms with large porch
Owensboro
9.6 out of 10, Exceptional, (45 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 AU$266
includes taxes & fees
25 Oct - 26 Oct
Bluegrass Bungalow 2 bedrooms with large porch
A modern kitchen with a TV, bar stools, and a trash can.

4. 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 AU$372
includes taxes & fees
26 Oct - 27 Oct
The Blue Herron of Carpenters Lake
A bedroom with a wooden ladder, a dresser, a wall-mounted TV, and a window with blinds.

5. 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)
"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...
United States
Barbara B.
The price is AU$495
includes taxes & fees
29 Oct - 30 Oct
Get ready for a Spellbinding Themed Getaway at Owensboro!
A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

6. Downtown Dream in Owensboro Ky

Downtown Dream in Owensboro Ky
Owensboro
9.4 out of 10, Exceptional, (25 reviews)
"Everything was great, perfect location downtown. "
United States
James K.
The price is AU$642
includes taxes & fees
26 Oct - 27 Oct
Downtown Dream in Owensboro Ky
A patio with a round table and chairs, surrounded by potted plants and a brick wall.

7. Bluegrass Vintage

Bluegrass Vintage
Owensboro
The price is AU$355
includes taxes & fees
22 Nov - 23 Nov
Bluegrass Vintage
A living room with a fireplace, a ceiling fan, and a flat-screen TV.

8. 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 AU$303
includes taxes & fees
25 Oct - 26 Oct
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A wooden observation tower with a small deck and stairs, surrounded by trees.

9. Charming Treehouse with Lake View and Access

Charming Treehouse with Lake View and Access
Utica
9.8 out of 10, Exceptional, (123 reviews)
"Awesome place to have some time with family away from everyone."
United States
Lori
The price is AU$219
includes taxes & fees
25 Oct - 26 Oct
Charming Treehouse with Lake View and Access
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 AU$337
includes taxes & fees
1 Nov - 2 Nov
Cozy Cottage home
A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

11. 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 AU$435
includes taxes & fees
27 Oct - 28 Oct
1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
A modern kitchen with a central island, bar stools, and pendant lighting.

12. The Bluegrass · 1 Bed · 1 Bath · 900 SF

The Bluegrass · 1 Bed · 1 Bath · 900 SF
Owensboro
The price is AU$597
includes taxes & fees
3 Nov - 4 Nov
The Bluegrass · 1 Bed · 1 Bath · 900 SF
A bowl on a woven placemat, a sofa with a pillow that reads 'River City,' and a wall with a partial view of a window.

13. River City Retreat | Stylish 1BR/1BA Apartment

River City Retreat | Stylish 1BR/1BA Apartment
Evansville
8.8 out of 10, Excellent, (6 reviews)
"Great stay, lots of food options, & very comfortable duplex"
United States
Nicholas S.
River City Retreat | Stylish 1BR/1BA Apartment
A living room with blue walls, a ceiling fan, a large clock, a massage chair, a massage table, and a patterned rug.

14. 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 AU$366
includes taxes & fees
25 Oct - 26 Oct
Welcome to simple comfort a like new family friendly home Full of accommodation
A neatly made bed with rolled towels, a patterned throw, and a yellow pillow.

15. RiverStone Retreat A

RiverStone Retreat A
Newburgh
8.8 out of 10, Excellent, (3 reviews)
"The host was very prompt on his responses. The apartment was very well maintained and clean. There are only a couple of glasses so that would be the only thing I'd change. Overall great experience. Me and my partner want to stay next time we get a VRBO 10/10"
United States
Unspecified U.
RiverStone Retreat A
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

16. 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 AU$430
includes taxes & fees
17 Nov - 18 Nov
The Bluegrass Barbie
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

17. 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, (2 reviews)
"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 AU$563
includes taxes & fees
28 Oct - 29 Oct
The Cowboys Slumber' 2 Mi to Lincoln State Park
A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

18. 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 AU$486
includes taxes & fees
26 Oct - 27 Oct
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.

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

Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
Owensboro
The price is AU$512
includes taxes & fees
29 Oct - 30 Oct
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
A wooden interior with a television, wooden cabinets, and a plant.

20. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"Doug is a wonderful host who goes the extra mile to make sure you are comfortable and enjoy your stay. His property is amazing, clean, and quiet. This was our third stay and we will definitely be back again and again."
United States
tasha k.
The price is AU$263
includes taxes & fees
25 Oct - 26 Oct
Guest House with acreage to explore.
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

Howard Johnson by Wyndham Evansville East

Howard Johnson by Wyndham Evansville East

10/10 Excellent
"This is our 3rd or 4th stay at this HoJo. The facility is always clean and quiet. The showers are looking older with some cracking of the walls. No bugs!!"
WILLIAM 2-night trip
Posted less than an hour ago
Howard Johnson by Wyndham Evansville East

Find out more about Rockport

Everything you need to know about Rockport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rockport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rockport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rockport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rockport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockport holiday rentals we have selected for you start as low as AU$219 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rockport rentals

At Expedia, we put the best Rockport holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rockport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rockport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rockport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.