Holiday rentals in Lewisport

Lakeside Cottage

Perfect for couples, thoughtfully designed with a soothing, rustic chic asthetic. Enjoy the wildlife, beautiful views and gorgeous sunsets from the tree tops! Propane fire pit on deck & wood fire pit in the yard with wood provided. Lots of places to relax around the property. About a 15 min drive into Owensboro which is a very cool year-round Rivertown! Be sure to check out Friday after 5:00 on the riverfront! if you're coming on a Friday! Let us know if you are bringing kayaks or canoes please!

The Storehouse - unique retreat near Holiday World

The Storehouse, a church built in the 1890s, is nestled in the serene backdrop of Grandview, Indiana. This former sanctuary has been thoughtfully transformed into a 3 BR home, perfectly blending old-world charm with contemporary amenities. You will love the original hardwood floors and stained glass windows in every room. Less than 15 min. from Holiday World and Lincoln State Park, there is much to do. Return and unwind in the private hot tub or gather around the fire pit under the stars.

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

Geno and Rocco's at Rough River, Lake Front Cabin

Escape to this cozy 2-bedroom, 1-bath cabin at Rough River Lake! Sleeping 6 with 3 beds, it overlooks the river banks and offers a fire pit area, picnic table, and a front porch with rocking chairs. The kitchen is fully stocked with all new pots, pans, dishes, and a coffee maker. Enjoy the provided indoor/outdoor games, bikes, books, fishing, kayaking, and a nearby golf course. Smart TV'S and high-speed WiFi for streaming available. Need something else? —just ask! As always pets are welcome.

Beech Hall Corner

This 1930s farmhouse sits on 2 acres just minutes from the Ohio River. It is the perfect place for those looking to slow down and enjoy the much simpler life in a rural area. The farmhouse has two bedrooms, one bath, full kitchen and a laundry room. Sit on the front porch and enjoy your morning coffee watching cars, jeeps, and motorcycles as they make their way along the Ohio River Scenic Byway. It also has a large rear deck, perfect for relaxing with a drink in hand overlooking the grounds.

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.

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.

Hattie's Hill Cottage

Cozy cottage located just behind the main home on the property (see photos). Relax by the pool, open seasonally, which is shared by the main house guests and host family, or enjoy an evening stroll out in the country. Conveniently located near Owensboro, Rockport, Hawesville, and Lewisport. The cottage features one flexible bedroom with either two twins or one California king, TV, well-stocked kitchen, dining/work space, comfortable recliners, and access to the beautiful grounds.

Feel at Home at the Highlander Center

Welcome to our three bedroom, two bath apartment in downtown Hawesville, Kentucky. It is tucked away in the back of a building that used to be the local school's bus garage. The mattresses are memory foam (Nectar), 42 inch smart TVs in every bedroom, and a 50 inch smart TV in the living room. A fully equipped kitchen with a dishwasher, washing machine, and dryer will make your stay more enjoyable. Free parking that is next to the entry door and lit by a street light. Free Wifi.

The Blue Heron of Carpenters Lake

Welcome to your peaceful lakeside escape. This cozy home has two bedrooms that sleep up to 6 guests and 1 full bathroom, thoughtfully designed for relaxation and comfort. Wake up to amazing lake views, unwind by the water and enjoy endless activities year around from summer swims, hiking, kayaking, games in the garage, or evening relaxing on the patio. Whether you’re seeking adventure or quiet moments by the lake, this home is an ideal place to stay to slow down and recharge.

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.

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.