Vacation rentals in Owensboro

4.97 out of 5 average rating, 145 reviews

A sliding door opens onto a spacious deck, framed by a wrought iron screen. Outdoor seating is positioned on the deck, facing a green yard and trees, allowing for a serene view of nature.

Loft in Hartford

Cozy One Bedroom Apartment in the Country

What was originally a hay loft has been converted into a country chic barn apartment. We would love to host you and your friends and family (including actual kids and fur kids) on our property. Children love collecting eggs from the chicken coop and everyone loves a short hike to the creek. We are only an hour from Mammoth Cave National Park and an hour from Holiday World in Santa Claus Indiana. The local community has charming little shops, several restaurants, and The Beaver Dam amphitheater.

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, 117 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.

The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.

4.96 out of 5 average rating, 139 reviews

The Cozy Cottage

Join us for a relaxing stay at the Cozy Cottage! Inside you will find everything you need to make for a cozy stay whether you’re with us for short weekend or a month. Outside you will find plenty of spaces to sit and enjoy the view of the Ohio River just 2 blocks away. The Cozy Cottage is conveniently located less than 5 minutes from downtown Owensboro and popular attractions such as the Convention Center, Bluegrass Museum, Botanical Gardens, and Jack C. Fisher Park.

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, 153 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.

4.96 out of 5 average rating, 168 reviews

The cottage features a welcoming front porch adorned with red shutters and a bright red door. Two large, round rocking chairs are positioned on the porch, surrounded by greenery and a blue planter. The pathway leads to the spacious entrance.

Cottage in Maceo

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 ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi. We have a Smart TV you may use your Netflix and so on with. Kitchen is well stocked with necessities. Eating/work space is provided. Comfortable recliner chairs. Access to the grounds.

4.97 out of 5 average rating, 386 reviews

A charming cottage is nestled among tall trees, surrounded by lush greenery. A stone pathway leads from the foreground to the front steps, which are framed by well-maintained landscaping and vibrant foliage. Sunlight filters through the leaves, creating a serene outdoor setting.

Cottage in Owensboro

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.

Vacation home in Owensboro

A spacious kitchen features wooden cabinets and a granite countertop island. Four wooden dining chairs surround a rectangular table. A door leads outside, and natural light enters through two windows dressed with light curtains.

4.92 out of 5 average rating, 131 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.

A tidy living room showcases a plush, purple sofa and a cozy armchair, accompanied by a decorative lamp and coffee table. A white fireplace serves as a focal point, while natural light filters through the window coverings, creating a welcoming ambiance.

4.98 out of 5 average rating, 163 reviews

Granny Smith's

Granny Smith's is an endearing home in the heart of Owensboro, located in a historic neighborhood. The house features one sizable bedroom, tidy living room, full kitchen, cozy dining area, and a tub/shower bathroom. There is also relaxed outdoor living areas either on the front porch or back screened in patio. Property also has a small detached carport with a driveway. There is also parking on the street.

A stylish living area features a light gray sofa and decorative pillows, complemented by a plush area rug. A gold bar cart displays various items, while a ceiling fan adds a functional touch. Distinct wall colors create a cozy atmosphere, and natural light brightens the space.

4.86 out of 5 average rating, 152 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!

The front exterior of the cottage features a welcoming entrance highlighted by a decorative wreath on the door. Two symmetrical windows are positioned on each side of the entrance, surrounded by well-maintained landscaping, including colorful flower beds and neat shrubs. A stone pathway leads to the door.

4.95 out of 5 average rating, 224 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.

A living room features hardwood floors and blue accent walls. Comfortable seating is provided by a sofa and two chairs, with a patterned area rug at the center. Natural light enters through a large window, and a fan hangs from the ceiling, enhancing the space's openness.

4.89 out of 5 average rating, 178 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 (per visit) of $45 paid through Airbnb. No more than two dogs and we ask that animals not sleep or be on the beds. Thank you!

A light-filled living area features a soft gray sofa adorned with textured cushions. A coffee table sits nearby on a patterned area rug, while a plush bean bag offers additional seating. Windows allow natural light to brighten the space, enhancing its inviting feel.

4.98 out of 5 average rating, 125 reviews

Newly renovated- 2.5 mi to Downtown Riverfront

The City House is a renovated 4 bed / 2.5 bath home in the heart of Owensboro. The convenient location makes it easy to get to restaurants, shopping, parks, downtown or sporting events. In less than 10 minutes, you can enjoy just about everything Owensboro has to offer whether it’s barbecue, bourbon or Bluegrass!

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Owensboro vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Owensboro

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, 93 reviews

The Bluegrass House

5 out of 5 average rating, 26 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

Superhost

A comfortable living area features a plush gray sofa and an accent chair, both positioned to invite relaxation. Natural light filters through a large window, complemented by light curtains. A decorative rug and a small lamp add subtle warmth to the space.

4.79 out of 5 average rating, 19 reviews

Cozy 2bd house next to hospital

5 out of 5 average rating, 40 reviews

A rustic cottage is nestled among trees, featuring a wood-paneled exterior. A small staircase leads to the entrance, adorned with potted plants. The surrounding greenery enhances the serene atmosphere, while the lake is visible in the background.

Cabin in Maceo

Lakeside Cottage

A spacious living area is highlighted by light wood flooring and neutral wall colors. A sectional couch is positioned around a coffee table on a patterned area rug. A dining set for six is visible in the background, with a ceiling fan illuminating the room.

5 out of 5 average rating, 27 reviews

Heartland Hideaway

Superhost

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

5 out of 5 average rating, 3 reviews

Rustic Log Cabin Old Farm

A charming exterior of a one-story home is visible, featuring a neatly landscaped front yard with grass and small shrubs. The light grey siding complements the simple design, while a concrete pathway leads to the front door, framed by two windows. A carport is seen on the side.

4.97 out of 5 average rating, 29 reviews

Cozy Retreat, modern Amenities

A single-story brick home with a brown, shingled roof is set against a clear blue sky. Lush green shrubs frame the entrance, and a manicured lawn leads to a two-car garage. A small decorative figure is positioned near the flowerbed, adding a subtle touch to the exterior.