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Holiday houses 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

4.84 out of 5 average rating, 202 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 Beaver Dam

4.95 out of 5 average rating, 257 reviews

Country Charm

This House is located in a quiet neighborhood one block of Main street here in Beaver Dam, KY. Enjoy a nice cozy country home while you visit. It is fully finished so you will feel right home. The property sits on a corner lot with access from both streets. The house has a front porch for lazy evening to catch some fresh air. You can pull right up underneath the carport for easy access to the back door for entry. The home offers a nice yard and fire pit. You are minutes from stores/ food.

Guest favourite

Home in Owensboro

5.0 out of 5 average rating, 129 reviews

4beds near 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, restaurants, and shopping, 30 min to Holiday world, private backyard with lighted patio. - Wifi - Roku Tv's in the living and all bedrooms - Washer and Dryer - Stocked kitchen.

Guest favourite

Cottage in Owensboro

4.98 out of 5 average rating, 99 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, 148 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

5.0 out of 5 average rating, 101 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, 330 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

Home in Owensboro

4.95 out of 5 average rating, 130 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

Loft in Newburgh

4.98 out of 5 average rating, 155 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. 2 complimentary drip coffees are included with your stay.

Guest favourite

Home in Owensboro

4.94 out of 5 average rating, 143 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

Farm stay in Owensboro

4.98 out of 5 average rating, 133 reviews

The Farmhouse on Nannie Belle

Set on 13 acres, this 142 year old Farmhouse will take you back to simpler times. Unplug and spend quality time with your family. Roast marshmallows, go fishing, play board games, or challenge your family to an intense game of foosball. A perfect place for families to reconnect. Note: The farmhouse road name has changed from Old Hwy 144 to Nannie Belle Loop.

Guest favourite

Home in Owensboro

4.93 out of 5 average rating, 184 reviews

Riverview Escape

Great location, newly decorated , right on the river with awesome river view. 5 minutes from the redeveloped downtown /Owensboro Convention Center/ International Bluegrass Museum / Smothers Park. Walking distance to flea markets. Free WIFI and cable TV. (THIS IS A NON SMOKING HOUSE.)

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Popular amenities for Owensboro holiday rentals

Free parking on premises

Air conditioning

Stay near Owensboro's top sights

Smothers Park14 locals recommend

Owensboro Convention Center4 locals recommend

Moonlite Bar-B-Q Inn18 locals recommend

Malco Owensboro Cinema Grill3 locals recommend

Old Hickory Bar-B-Que8 locals recommend

Bluegrass Music Hall of Fame & Museum17 locals recommend

Other great holiday rentals in Owensboro

Home in Owensboro

4.83 out of 5 average rating, 71 reviews

Adorable two bedroom two bath entire home

Guest favourite

Home in Owensboro

4.91 out of 5 average rating, 66 reviews

Comfortable 2 bedroom with 2 private baths, patio.

Guest favourite

Cottage in Owensboro

4.97 out of 5 average rating, 70 reviews

Cottage with Screened Porch in Owensboro

Guest favourite

Home in Owensboro

4.91 out of 5 average rating, 56 reviews

The Cozy Cottage

Guest favourite

Apartment in Owensboro

4.9 out of 5 average rating, 92 reviews

Bluegrass Bungalow 2 Bdr/1 Bath with Large Porch

Guest favourite

Home in Owensboro

4.9 out of 5 average rating, 40 reviews

Naomi's Gnome Home

Guest favourite

Apartment in Owensboro

5.0 out of 5 average rating, 22 reviews

River House Suite

Guest favourite

Home in Owensboro

4.94 out of 5 average rating, 67 reviews

Bluegrass Commons

Quick stats about accommodation in Owensboro

Total rentals
100 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
4.7K reviews
Nightly prices starting at
$61 AUD before taxes and fees

Destinations to explore