Holiday houses in Owensboro

4.85 out of 5 average rating, 226 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!

4.96 out of 5 average rating, 167 reviews

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 (Pool is currently under repair) 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.

4.94 out of 5 average rating, 113 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.

Superhost

Apartment in Owensboro

4.84 out of 5 average rating, 110 reviews

My Old Kentucky Home: Downtown Stylish 1 Bedroom

A few minute walk to Downtown Owensboro! Welcome to our charming Airbnb in Owensboro, KY! Experience modern comfort and historic charm in the heart of the city. Relax in the cozy living area, cook in the fully equipped kitchen, and enjoy a peaceful night's sleep in the comfortable bedroom. Explore nearby attractions, indulge in local cuisine, and make unforgettable memories. Only a few blocks from Smothers Park, Bluegrass Museum, and more! Book now for an exceptional stay!

4.96 out of 5 average rating, 135 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.

5 out of 5 average rating, 147 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.

4.97 out of 5 average rating, 382 reviews

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.

Holiday home in Owensboro

4.92 out of 5 average rating, 128 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.

Superhost

Cabin in Dixon

4.9 out of 5 average rating, 500 reviews

Handcrafted Cabin in Woodsy Heaven

Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

4.85 out of 5 average rating, 148 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!

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.

4.98 out of 5 average rating, 138 reviews

Bungalow in Owensboro

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.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Houses

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

Popular amenities for Owensboro holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Owensboro

4.9 out of 5 average rating, 92 reviews

The Bluegrass House

ScottRating, 5 stars3 weeks ago

Wonderful Hospitality. Big thanks to KEVIN

5 out of 5 average rating, 13 reviews

Cabin in Owensboro

Poolside Serenity Cabin

HeidiRating, 5 stars3 weeks ago

Loved our stay here. Place was easy to find. It was nice and clean. Lori and her husband were very nice and chatty. Very responsive too! It was a wonderful home away from home! Would recommend and do plan on staying here in future visits!

4.94 out of 5 average rating, 33 reviews

house with king bed

PickyRating, 5 stars6 days ago

This Airbnb was exactly what we needed after a long day at a convention—quiet, cute, and in a neighborhood that felt safe and welcoming. The pictures matched perfectly, and it was super easy to get in. Everything we needed, including the convention center, was within 15 minutes. A great stay all around!

5 out of 5 average rating, 18 reviews

Green River Getaway

JeffRating, 5 stars4 days ago

Beautiful updated home! Had high end appliances, tastefully decorated and very clean and comfortable. Beds were super comfortable! Loved the great water pressure.Enjoyed the big screen tvs. Outside was very manicured. Enjoyed the big covered porch as it rained a lot. Big dock and fire pits with wood our favorite Saw an eagle salamanders and a toad. Thanks so much for having us! God bless! Jeff and Mike

5 out of 5 average rating, 81 reviews

Guest suite in Owensboro

Quiet Country Views

JohnRating, 5 stars1 week ago

This place is just a few miles outside of town and so worth it. Beautiful farmland. Beautiful home. Spacious rooms. I wish we could’ve stayed longer to maybe make use of the beautiful surroundings by sitting around the fire pit. Hosts are super friendly and always available to respond to any questions. We had zero issues.

5 out of 5 average rating, 25 reviews

Heartland Hideaway

JoshuaRating, 5 stars1 week ago

2nd time staying at this location. Nice, private home. Perfect for my extended stay in Owensboro. I will stay here again in the future.

4.94 out of 5 average rating, 64 reviews

Barn in Philpot

Fiddlewood Farm Barn Stay

JoAnnRating, 5 stars3 weeks ago

Another great stay at Fiddlewood Farm! Shelly is a wonderful host! Very nice and responsive! Their farm is peaceful and relaxing! Can’t wait for our next stay!