Holiday rentals in Owensboro

4.97 out of 5 average rating, 143 reviews

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.

4.96 out of 5 average rating, 166 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.

4.97 out of 5 average rating, 139 reviews

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.

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.

5 out of 5 average rating, 172 reviews

4beds3BR/30to HolidayWorld/near Conv Ctr/Fisher Pk

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv, private Home is 3 miles from 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 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.

4.88 out of 5 average rating, 244 reviews

Bungalow in Owensboro

The Green Garden Cottage

The Cottage House is centrally located to library and 1 1/2 miles from Riverfront. This 1930s home has hardwood floors, glass door knobs, and rounded entry ways. The kitchen has been remodeled with new appliances, cabinets and countertops. The upstairs bedroom is a large finished attic with its own heating and cooling system. 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.

4.96 out of 5 average rating, 134 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, 381 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

4.93 out of 5 average rating, 127 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

4.85 out of 5 average rating, 146 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!

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

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

Popular amenities for Owensboro holiday rentals

Kitchen

Wifi

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 stars2 weeks ago

Wonderful Hospitality. Big thanks to KEVIN

5 out of 5 average rating, 22 reviews

Home in Olaton

Cowbell Cottage farm stay

JayneseRating, 5 stars1 week ago

Tracy‘s place was beautiful and exactly as described… It had everything we needed! It was just so peaceful and thoughtfully decorated!

5 out of 5 average rating, 15 reviews

Cabin in Hardinsburg

Rough River Oasis: Close to Lake - Deck - Fire Pit

TonyaRating, 5 stars3 weeks ago

Sarah’s place was exactly as described. My favorite part was the coffee bar! I love my coffee! Everything was very clean and the kitchen was well stocked. Sarah was very quick to respond with any questions I had. We had a great time celebrating my husband’s 40th! We went and played disk golf, mini golf, and ate at porgies. It was a great relaxing time! This is a great location for a quiet and relaxing getaway.

5 out of 5 average rating, 81 reviews

Guest suite in Owensboro

Quiet Country Views

JohnRating, 5 stars2 days 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, 52 reviews

Blue Moon Cottage: Music Room, Inground Pool

KimberlyRating, 5 stars3 weeks ago

We really enjoyed our stay at Blue Moon Cottage. Matt and Angel were amazing with their communication. Beautiful home. Perfect for 2 families traveling for a quick getaway. We loved the pool and quiet neighborhood. Hope to be back soon!

5 out of 5 average rating, 25 reviews

Heartland Hideaway

JoshuaRating, 5 stars2 days 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.

5 out of 5 average rating, 27 reviews

Home in Calhoun

The Nest

TiffanyRating, 5 stars3 weeks ago

Ethan’s home was so clean and beautiful! The quiet countryside was just what we were looking for! He was always quick to respond and extremely friendly! Would recommend this place to anyone!