Vacation rentals in Philpot

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Top-rated vacation rentals in Philpot

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The exterior of a single-story home features light gray vinyl siding and a dark gray roof. White window shutters complement the windows, and a covered porch is positioned at the entrance. A grassy lawn surrounds the house, with a clear sky and scattered clouds above.

Home in Owensboro

4.84 out of 5 average rating, 230 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!

Top guest favorite

A sliding door opens onto a spacious deck, framed by a wrought iron screen. Outdoor seating is positioned on the deck, facing a green yard and trees, allowing for a serene view of nature.

Loft in Hartford

4.97 out of 5 average rating, 150 reviews

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.

Guest favorite

The exterior of a renovated two-story home is featured, showcasing a distinct architectural design with exposed beams. Large windows allow natural light to enter, while a welcoming front door is framed by decorative lighting fixtures. A concrete pathway leads to the entrance.

Cottage in Owensboro

4.97 out of 5 average rating, 141 reviews

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.

Guest favorite

The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.

Home in Owensboro

4.96 out of 5 average rating, 150 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.

Guest favorite

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

4.96 out of 5 average rating, 171 reviews

Hattie's Hill Cottage

Cottage sits behind our home (see photo). NOTE- Main house may have large groups. Pool and outside areas share spaces. 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.

Guest favorite

An outdoor deck features a rectangular table with a central hole for an umbrella, surrounded by four wicker chairs. Lush greenery and trees provide a natural backdrop, with a peaceful lake visible in the distance.

Cottage in Huntingburg

4.86 out of 5 average rating, 238 reviews

Lakeside Cottage Getaway Fishing, Hiking, Relaxing

Enjoy the lovely setting of this romantic spot in nature. This quiet getaway comes with a full kitchen, two bedrooms, access to a lovely lake, and an outdoor deck for enjoying the view. The master bedroom has a queen size bed and a crib. The second bedroom has a twin bed and a bunk bed [twin over full]. This space is perfect for singles, couples, or even large families. Close to Patoka Lake and Holiday World. No smoking/not handicap accessible

Top guest favorite

A charming cottage is nestled among tall trees, surrounded by lush greenery. A stone pathway leads from the foreground to the front steps, which are framed by well-maintained landscaping and vibrant foliage. Sunlight filters through the leaves, creating a serene outdoor setting.

Cottage in Owensboro

4.97 out of 5 average rating, 392 reviews

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.

Top guest favorite

A tidy living room showcases a plush, purple sofa and a cozy armchair, accompanied by a decorative lamp and coffee table. A white fireplace serves as a focal point, while natural light filters through the window coverings, creating a welcoming ambiance.

Home in Owensboro

4.98 out of 5 average rating, 168 reviews

Granny Smith's

Granny Smith's is an endearing home in the heart of Owensboro, located in a historic neighborhood. The house features one sizable bedroom, tidy living room, full kitchen, cozy dining area, and a tub/shower bathroom. There is also relaxed outdoor living areas either on the front porch or back screened in patio. Property also has a small detached carport with a driveway. There is also parking on the street.

Guest favorite

A stylish living area features a light gray sofa and decorative pillows, complemented by a plush area rug. A gold bar cart displays various items, while a ceiling fan adds a functional touch. Distinct wall colors create a cozy atmosphere, and natural light brightens the space.

Home in Owensboro

4.85 out of 5 average rating, 159 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!

Top guest favorite

The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.

Loft in Newburgh

4.98 out of 5 average rating, 304 reviews

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.

Top guest favorite

A bright kitchen features a wooden countertop with an egg carton holding various eggs. A window allows natural light to illuminate the space, and fresh flowers are seen in a glass vase. Decorative signs and a small sink complement the clean design.

Farm stay in Owensboro

4.98 out of 5 average rating, 150 reviews

The Farmhouse on Nannie Belle

Set on 13 acres, this 142 year old Farmhouse will take you back to simpler times. Unplug and spend quality time with your family. Roast marshmallows, go fishing, play board games, or challenge your family to an intense game of foosball. A perfect place for families to reconnect. Note: The farmhouse road name has changed from Old Hwy 144 to Nannie Belle Loop.

Top guest favorite

A light-filled living area features a soft gray sofa adorned with textured cushions. A coffee table sits nearby on a patterned area rug, while a plush bean bag offers additional seating. Windows allow natural light to brighten the space, enhancing its inviting feel.

Home in Owensboro

4.98 out of 5 average rating, 133 reviews

Newly renovated- 2.5 mi to Downtown Riverfront

The City House is a renovated 4 bed / 2.5 bath home in the heart of Owensboro. The convenient location makes it easy to get to restaurants, shopping, parks, downtown or sporting events. In less than 10 minutes, you can enjoy just about everything Owensboro has to offer whether it’s barbecue, bourbon or Bluegrass! We are also 40 minutes from Holiday World.