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Near Holiday World & Owensboro, The Little House

The Little House is a charming 2-BR, 1-bath retreat, ideal for family vacations or romantic getaways. Nestled in a peaceful location, this cozy home offers easy access to local attractions: Lincoln Pioneer Village and Museum – 0.3 miles Downtown Owensboro – 10 miles Bluegrass Hall of Fame – 11 miles Newburgh, IN – 21 miles Holiday World – 21 miles Unwind and relax in this convenient, comfortable home base. Pet-friendly for small dogs under 25lbs (Pet fee: $50). Professional photos coming soon!

Lakeside Cottage

Perfect for couples, a private getaway that feeds your soul and connects you to nature! Enjoy the wildlife, beautiful views and gorgeous sunsets from the tree tops! Only a 15-20 minute drive to downtown Owensboro, a rivertown hosting year-round events, and fantastic eateries and shopping. We offer a special sweet treat for birthdays, anniversaries, honeymoons and baby moons! We have a small dock for all day coming and going. bring your own kayaks or canoe! Being on the water here is amazing!

Bluegrass Run- Sleeps 8 & Cozy Stay

Relax and unwind in this charming 3-bedroom, 2-bath retreat located just 8 minutes from downtown. Step inside to a warm and inviting living space featuring a sleeper sofa, perfect for accommodating extra guests. The home is thoughtfully furnished with modern touches and all the essentials for a comfortable stay. The upstairs master bedroom offers added privacy, while the two additional bedrooms provide a calm and cozy atmosphere. With 2 bathrooms, mornings are easy and convenient for everyone.

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.

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).

Green River Getaway

Experience relaxation and adventure at the Green River Getaway. Nestled right on the banks of the Green River. Our property offers beautiful views. Enjoy mornings and sunsets from your own private dock. Our outdoor area is ideal for gatherings or intimate events. Fire pits are available and so is firewood so you can focus on making memories not worrying about supplies. Whether you're hosting a special event (with prior approval) or a peaceful retreat, our property provides the perfect place!

Woodsy Waterfront Cabin with Loft

Escape to our secluded waterfront cabin, nestled amidst natural surroundings, our cabin offers a serene retreat away from the hustle and bustle of everyday life. Wake up to the soothing sounds of nature and breathtaking views of the water. Whether you're seeking a romantic getaway or a peaceful retreat with loved ones, our cabin provides the perfect setting for relaxation and rejuvenation. Experience the magic of nature at its finest in this special haven. WiFi is available and included.

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.

Tranquil & Modern Sanctuary

I rent my home part time while travelling for work. It’s fully renovated with a minimalist design. The master bedroom has a king-size memory foam mattress and attached bath. Down the hall is a guest bedroom with queen-size bed, small TV, and bathroom across the hall. The L-shaped living room has a large TV, sectional seating, and dining area. The kitchen is fully equipped for cooking. The house has a great central location with quick access to downtown, Legion Park, and the bypass.

Centrally located 3 bdrm quaint house with a yard

No cleaning fee! 3 bdrm (5 beds), 2 full bath house with a yard. Outdoor dining area with a grill and fire pit. .5 mi from Legion Park, a 22 acre space with playground, picnic shelters, basketball & tennis courts. 2.9 miles from the Owensboro Riverfront with Smothers park named "Top playground in the World", fountains, restaurants, shopping and depending on the time of year activities and concerts. Also located riverfront is the Bluegrass Music Hall of Fame & Museum.

Hot Tub on Hill Sleeps 12 | POOL|Hot Tub & Firepit

Welcome to the Hot Tub on Hill . Nestled in the center of town. This stylish group-friendly Airbnb sleeps 12 and is perfect for family reunions, wedding groups, golf trips, corporate stays, or families relocating. Enjoy two spacious living areas, upscale furnishings, and a private backyard retreat with pool, hot tub, firepit, gas grill, and full outdoor seating—designed for relaxing and entertaining. Close to downtown events , restaurants , 40 min to Holiday World .

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.