Vacation rentals in Philpot

4.97 out of 5 average rating, 144 reviews

A set of wooden stairs leads up alongside a red metal building, framed by a railing with a wire mesh design. The stairs, slightly worn, are surrounded by greenery, providing access to the upper level of the barn apartment.

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, 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 (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.

An open-concept living area is highlighted by modern furnishings and natural light. A sectional sofa is paired with a circular coffee table, while a well-equipped kitchen with bar seating is visible in the background. Stylish artwork complements the neutral color palette.

4.94 out of 5 average rating, 115 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.

4.98 out of 5 average rating, 101 reviews

Treehouse in Lewisburg

Aerial Joy Treehouse(Lake Malone)

Prepare to be taken to new heights as you enjoy this beautiful, private treehouse located on Lake Malone. It features an absolutely stunning view of the lake through an 8x14 glass door that opens up to allow the cool lake breezes to waft your cares away as you relax in the recliner. It also features a large deck, full kitchen, Jacuzzi tub, rainfall shower, beautiful woodwork, two complimentary kayaks, and many other unique features that will make your stay unforgettable.

A wide view of a calm river scene is presented, with a grassy slope leading down to the water. A boat is docked near the shore, while individuals can be seen walking along the pathway. The sky is clear with a few scattered clouds.

4.96 out of 5 average rating, 136 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 kitchen space is presented, featuring dark cabinetry and a speckled granite countertop. A coffee maker sits prominently on the counter beside decorative items. Natural light enters through a nearby door, highlighting the organized shelves with baskets and a welcome sign.

4.99 out of 5 average rating, 150 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, 385 reviews

Lush trees with vibrant green and yellow leaves create a canopy in a tranquil forest. Sunlight filters through the branches, illuminating the forest floor covered in fallen leaves. The scene conveys a serene natural environment, ideal for exploration and relaxation.

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.

A marble-topped coffee table displays a stack of vintage records alongside a book titled 'Doodle Revolution.' The records, with colorful labels, are arranged in a casual yet appealing manner on the soft, patterned rug.

4.85 out of 5 average rating, 151 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!

4.98 out of 5 average rating, 281 reviews

A two-story building features a spacious deck with a railing, overlooking the river. A staircase leads to the upper entrance, while a small seating area with colorful chairs is visible by the shoreline. The sky displays soft pink and orange hues at sunset.

Loft in Newburgh

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. 2 complimentary drip coffees are included with your stay.

4.97 out of 5 average rating, 112 reviews

A serene view of a river stretches out under a colorful sky, reflecting the greenery along the banks. A bridge spans the water in the distance, framed by trees showing hints of seasonal color. The riverbank is lined with grass and natural rock formations.

Home in Livermore

River Trails Inn

Historic two story home with three bedrooms and 3 1/2 baths, circa 1900, located in the old downtown district of the quaint river town of Livermore, Kentucky, just two blocks from the confluence of the Green and Rough Rivers and our expansive riverfront recreation complex. River kayaking and canoeing and biking trails on marked low-use county roads are right in your back yard!!

A hallway featuring a light-toned rug runs alongside white cabinetry and multiple doors. A farmhouse-style sliding door is positioned at the end of the hall, contributing to the modern design. Natural light is provided by a stylish ceiling fixture.

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.