Holiday rentals in Whitesville

5.0 out of 5 average rating, 41 reviews

A peaceful countryside scene features rolling hills and a clear pond surrounded by trees. Bare branches indicate the changing seasons, while a vibrant blue sky is dotted with soft clouds, creating a serene backdrop of nature.

Home in Olaton

Cowbell Cottage farm stay

Welcome to Cowbell Cottage, a charming two-bedroom, one-bath retreat on a peaceful working cow farm. Built around an authentic 1800s log cabin, this home is restored with a cozy western theme, blending rustic charm with modern comfort. Relax in the tranquil countryside, where the sounds of nature replace city noise. While there’s no TV to interrupt the serenity, Wi-Fi is available for your convenience. Cowbell Cottage offers a unique getaway that celebrates history, and the beauty of farm life.

4.81 out of 5 average rating, 47 reviews

A hexagon structure is illuminated by string lights, featuring four swinging chairs arranged around a central fire pit. A stack of firewood is positioned nearby on a gravel surface, surrounded by trees that create a secluded outdoor atmosphere.

Barn in Philpot

Walk in the Woods - Pole Barn, Game-Room, Firepit

If you are looking to unplug, relax, and unwind this barndominium nestled in 93 acres of woods is the place for you. Enjoy the fully equipped kitchen, bathroom, three bedroom, wrap around porch and large garage area. The custom firepit w/ swings is the perfect place to spend the evening watching the stars and enjoying nature. This home boasts many amenities including disc golf, hiking trails, outdoor seating, foosball, ping pong table, corn hole boards and so much more. 3 camper hookups avail.

A spacious living area is furnished with a large sectional sofa, complemented by decorative pillows. A ceiling fan provides airflow, while natural light filters through the window blinds. A guitar hangs on the wall, and a wall-mounted artwork adds a pop of color.

4.9 out of 5 average rating, 136 reviews

The Bluegrass House

Welcome y'all! Serene hot tub, fenced-in back yard (2-dog limit, extra charge). Airport shuttle (separate fee). Nestled near parks, 3 miles from Edge Ice/Sports Arena. Immerse yourself in cultural richness at Bluegrass Music Hall of Fame and Owensboro Symphony Orchestra. Enjoy free summer outdoor entertainment on the Riverfront. Holiday World (30+min). Experience southern style with breakfast at Windy Hollow Biscuit House, & ribs, mutton or burgoo at Moonlight BBQ (visited by celebrities).

An open concept living area features a plush gray sofa with accent pillows, complemented by a modern coffee table on a textured area rug. The kitchen area includes wooden cabinets and bar seating, while natural light brightens the space through a nearby window.

5.0 out of 5 average rating, 196 reviews

4bed3BR 35 to HolidayWorld/Near Conv Ctr/Fisher Pk

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv! Home is 3 miles from Convention Ctr, Bluegrass Museum, Science Museum, Botanical Garden. It’s also 4 minutes from baseball fields (Fischer), Thompson Berry( soccer), 35min to Holiday world, private and fenced backyard with lighted patio. Home is well stocked with ALL you may need! If the home is empty previous night, early check in, no charge! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen, book now!

4.98 out of 5 average rating, 176 reviews

The exterior of a renovated two-story home is featured, showcasing a distinct architectural design with exposed beams. Large windows allow natural light to enter, while a welcoming front door is framed by decorative lighting fixtures. A concrete pathway leads to the entrance.

Cottage in Owensboro

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.

5.0 out of 5 average rating, 39 reviews

A rustic log cabin is set against a backdrop of greenery, with a large Osage Orange tree providing shade. The cabin features a combination of natural wood exteriors and a modern addition, showcasing a warm and inviting entrance surrounded by well-maintained landscaping.

Cabin in Utica

Rustic Log Cabin Old Farm

Step back in time at this 1800s log cabin on historic DeLacey Farm. Surrounded by barns, wildlife, and wide-open fields, this rustic getaway sits on a nearly 100-year-old working farm—just minutes from Owensboro’s BBQ, bourbon, and small-town charm. Relax on the back deck with views of the original farm buildings, or head into town to explore the Green River Distillery and local eats. It’s the perfect blend of peaceful retreat and convenient access to everything Owensboro has to offer.

A single-story home with a brick facade is presented. The driveway leads to a garage, while a well-maintained lawn features neatly trimmed grass and colorful flowerbeds. Large front windows allow for natural light, framed by light-colored siding underneath a gabled roof.

4.94 out of 5 average rating, 141 reviews

Bluegrass Commons

You will be close to everything when you stay at this centrally-located three bedroom two bath home right off the bypass that is a short drive to anywhere in Owensboro, KY for any business travelers. This is a brand new construction home in Bluegrass Commons neighborhood! New furnishings and the home sleeps 6 comfortably. Split bedroom with an open concept perfect for families. Fully stocked kitchen with a keurig coffee station. Large backyard perfect for entertaining or just grilling.

5.0 out of 5 average rating, 73 reviews

Village Cottage - 2BR King+Queen | 2 Baths | Patio

Welcome to your home away from home at The Village Cottage! While you’ll feel tucked away in a peaceful, family-friendly neighborhood, this cozy 2-bed, 2-bath home offers the perfect retreat for anyone visiting Owensboro. Within just a few minutes, you can reach the convention centre, downtown, hospital, grocery stores, cafes, restaurants, movie theatre, casino and the green belt. Whether you're in town visiting family & friends or on a business trip, we look forward to hosting you!

5.0 out of 5 average rating, 28 reviews

Flat in Owensboro

The Guest House at Kate & Waverly

Welcome to the Guesthouse at Kate & Waverly! This beautiful historic building, built in 1902, is located in downtown Owensboro. We are walking distance to many downtown restaurants and bars, as well as the Convention Center, Bluegrass Music Hall of Fame, Bluegrass Fieldhouse, and the beautiful Ohio riverfront and park. The AirBnB is located on the second floor above Kate & Waverly—a gift shop with unique vintage and antique finds, as well as an interior design center.

A spacious living area features a large flat-screen television mounted on a dark wall. Two light gray sofas are arranged around a round coffee table on a textured rug. Soft lighting from two side tables complements the warm wooden flooring.

4.99 out of 5 average rating, 198 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.

5.0 out of 5 average rating, 15 reviews

A spacious living area is highlighted by a large sectional sofa adorned with decorative cushions. A flat-screen TV is mounted on the wall, while a ceiling fan provides airflow. Natural light enters through an open doorway leading to a dining space, enhancing the inviting ambiance.

Flat in Owensboro

Bluegrass Hideaway

Cozy 2-bedroom, 1-bath retreat perfect for families, friends, or business travelers. Sleeps 4 comfortably with plush bedding. Fully equipped kitchen, spacious living area, high-speed WiFi, and Smart TV for entertainment. Fresh towels and toiletries provided. Free parking available. Conveniently located near restaurants, shopping, and local attractions. Experience comfort and convenience in a relaxing space. Book your stay today!