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Holiday rentals in Owensboro

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Top-rated holiday rentals in Owensboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Owensboro

4.83 out of 5 average rating, 218 reviews

Emma B's Place Close to Town and the Riverfront

Emma B's Place is newly renovated and ready for guests! Here you'll find a cozy atmosphere, comfortable beds, fully equipped kitchen, and brand new washer & dryer. The location is convenient to an award winning Riverwalk, shopping, great dining, and our central location offers a short commute to the entire city. If you prefer to stay in and relax, a 42-inch smart tv and wireless high-speed internet are available for your enjoyment. Lockbox self-entry. Your hosts live nearby if you need anything!

Guest favourite

Home in Owensboro

5 out of 5 average rating, 153 reviews

4beds3BR/Conv Ctr/Fisher pk/30 min Holiday World

CLEAN, updated 3 bedroom home, 4 beds each with tv, private backyard! This home is close (3 mi) to the downtown area featuring; Smothers Park & Playground right on the river front, Convention Center, River Park Center, Bluegrass Museum, Science Museum, Botanical Garden. It’s also minutes from baseball fields (Fischer) 30 min to Holiday world, private backyard with lighted patio. Home is well stocked with ALL you may need! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen.

Guest favourite

Cottage in Owensboro

4.97 out of 5 average rating, 118 reviews

The Woodford Retreat Cottage

Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

Guest favourite

Cottage in Maceo

4.97 out of 5 average rating, 158 reviews

Hattie's Hill Cottage

Cottage sits behind our home (see photo) . NOTE- Main house may have large groups ... pool and outside areas share spaces ...Near Owensboro, Rockport, Hawesville & Lewisport...There is ONLY ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi ..Smart TV... use your Netflix and so on with this TV ...... Kitchen has everything you need ..Eating/work space. Comfortable recliner chairs ... Use of pool/ plenty of places to roam on farm .

Guest favourite

Home in Owensboro

5 out of 5 average rating, 126 reviews

Midtown Cottage- Self Check-In & Centrally Located

Enjoy your stay in Owensboro, KY in this cozy, warmly decorated home! This home is centrally located to everything Owensboro has to offer, a short drive from downtown and the award winning riverfront. Wifi and parking are included. Enjoy a stylish experience at this centrally-located home. You will enjoy relaxing either in the home or the lovely backyard space. Whether you are in town for work or play indulge in the comfort and tranquility of this modern house.

Guest favourite

Cottage in Owensboro

4.97 out of 5 average rating, 363 reviews

Nature Lovers Retreat

This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

Guest favourite

Holiday home in Owensboro

4.93 out of 5 average rating, 109 reviews

The little big cozy house

The little big cozy house offers you a place where you can relax and feel at home. a spacious kitchen with all the necessary elements such as The 3 bedrooms ,that invite you to rest with very suitable beds For you to spend a magnificent and comfortable night. The patio is a space where you can enjoy a grill surrounded by family or friends. This house is an excellent location that gives you quick access to any part of owensboro.

Guest favourite

Home in Owensboro

4.95 out of 5 average rating, 138 reviews

Cottage by the River & Convention Center

Great little cottage located in the bustling newly renovated Riverfront. 3 Blocks from Convention Center & very near Bluegrass Music Hall of Fame & Museum, RiverPark Center Performing Arts, Owensboro Historical Museum, Owensboro Art Museum, Smother's Park, restaurants, shopping, churches & the Antique Mall. All in walking distance or get on the free trolley 2 blocks over. Free WIFI, Smart TVs, Free Street Parking.

Guest favourite

Home in Owensboro

4.88 out of 5 average rating, 119 reviews

The Bluegrass Barbie

Welcome to Owensboro, KY home to the ONLY Bluegrass Museum Hall of Fame on PLANET EARTH! Minutes away from Owensboro Convention Center, ALL sports facilities, world class dining, & one of the MOST UNIQUE stays in Owensboro, KY! Great home to stay at for sports tournaments, visiting family, visiting Holiday World, or just a weekend away! And don't forget to check out The Green River Distillery!

Guest favourite

Home in Owensboro

4.94 out of 5 average rating, 180 reviews

2 bedroom w/free on-site parking. Near downtown

When you stay at this centrally located accommodation, your family will be close to everything. The backyard is fenced in and has a fire pit. The sofa has one pullout bed. The master suite has one queen bed. The second bedroom has two XL twin beds. Complete kitchen with dishwasher, plates, utensils, and washer and dryer. No more than two pets. Pets must be under 30 pounds each.

Guest favourite

Bungalow in Owensboro

4.98 out of 5 average rating, 125 reviews

Bluegrass Bungalow: Historic Charm, Modern Comfort

Welcome to the Bluegrass Bungalow, a charming 1924 two-bedroom, one-bath home that seamlessly blends historic charm with modern amenities. Located near the Ohio River and downtown, this cozy retreat is just moments from top restaurants and shopping. Enjoy the preserved vintage details alongside a fully renovated kitchen and bath, including a spacious walk-in shower.

Guest favourite

Home in Owensboro

4.89 out of 5 average rating, 167 reviews

The Cabin in Town

The Cabin in Town is recently remodeled home from the 1950s with hardwood floors and original trim work. The house is centrally located in town on a nice quiet street and ready to receive guests. We do allow pets for an additional one-time fee of $45 paid through Airbnb. No more than two dogs and we ask that animals not sleep or be on the beds. Thank you!

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Popular amenities for Owensboro holiday rentals

Free parking on premises

Air conditioning

Stay near Owensboro's top sights

Moonlite Bar-B-Q Inn18 locals recommend

Bluegrass Music Hall of Fame & Museum17 locals recommend

Smothers Park14 locals recommend

Spirits at The Miller House9 locals recommend

O.Z. Tyler Distillery9 locals recommend

The Famous Bistro8 locals recommend

Other great holiday rentals in Owensboro

Guest favourite

Home in Owensboro

4.89 out of 5 average rating, 75 reviews

The Bluegrass House

Guest favourite

Home in Owensboro

4.97 out of 5 average rating, 34 reviews

3BR Near Convention Center & Parks, Close to fun!

Guest favourite

Home in Beaver Dam

5 out of 5 average rating, 60 reviews

Rise and Shine on Main

Guest favourite

Rental unit in Owensboro

4.91 out of 5 average rating, 22 reviews

The Farmers Loft- Second floor

Guest favourite

Home in Owensboro

5 out of 5 average rating, 16 reviews

The Farmhouse- 3 bedroom, 2 bath

Guest favourite

Home in Owensboro

4.96 out of 5 average rating, 52 reviews

Quite and Cozy on Deer Trail

Guest favourite

Home in Owensboro

4.95 out of 5 average rating, 22 reviews

Horse Haven at the Heartlands

Guest favourite

Cabin in Owensboro

4.97 out of 5 average rating, 33 reviews

Woodsy Waterfront Cabin with Loft

Quick stats about holiday rentals in Owensboro

Total rentals
110 properties
Nightly prices starting at
$54 SGD before taxes and fees
Total number of reviews
5.7K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Destinations to explore