Holiday rentals in Philpot

4.85 out of 5 average rating, 226 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!

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, 167 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.

4.94 out of 5 average rating, 114 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.

4.96 out of 5 average rating, 135 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.

4.99 out of 5 average rating, 149 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, 383 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.

4.85 out of 5 average rating, 149 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!

4.95 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.

4.98 out of 5 average rating, 138 reviews

Bungalow in Owensboro

Bluegrass Bungalow: Historic Charm, Modern Comfort

Welcome to the Bluegrass Bungalow, a charming 1924 two-bedroom, one-bath home that seamlessly blends historic charm with modern amenities. Located near the Ohio River and downtown, this cozy retreat is just moments from top restaurants and shopping. Enjoy the preserved vintage details alongside a fully renovated kitchen and bath, including a spacious walk-in shower.

4.98 out of 5 average rating, 149 reviews

Farm stay in Owensboro

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.

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Popular amenities for Philpot holiday rentals

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Other great holiday rentals in Philpot

Superhost

5 out of 5 average rating, 4 reviews

On Sale! Home Base East Side Hwy 54 with Garage

QuadeRating, 5 stars9 months ago

I stayed here for 2 months on a work trip, and loved my time at the house. Amy and cohost Jenny are very responsive and quick to address any issues that arise. Beautiful property with plenty of space. All amenities the you could need!

5 out of 5 average rating, 23 reviews

Home in Olaton

Cowbell Cottage farm stay

AmandaRating, 5 stars1 week ago

We absolutely LOVED our stay at the Cowbell Cottage! From the moment we arrived, our host Tracy went above and beyond to make us feel welcome – she was so kind and helpful. The cottage itself was spotless, beautifully decorated, and everything felt so fresh and new. The area is absolutely stunning and peaceful, yet just a quick 20-minute drive to the concert venue in Beaver Dam. The fresh eggs were such a sweet touch (and delicious – thank you, Tracy!), and let’s talk about those PILLOWS… hands down, the best sleep ever! Every detail of our stay was perfect. We can’t say enough great things about this little piece of paradise. We’ll absolutely be back!

4.98 out of 5 average rating, 50 reviews

Peaceful Stay | Relax & Unwind

GaryRating, 5 stars2 weeks ago

Great place to stay while we caught up with family

4.75 out of 5 average rating, 16 reviews

Cozy 2bd house next to hospital

AmyRating, 5 stars2 months ago

Great place to stay. close to whatever shops or stores you need. Close to Hospital. This is a older home that has been remodeled. spacious bedrooms, living room, and kitchen. Very small bathroom. Even though remodeled, still a little outdated. Many outlets didn't accommodate 3 prong plugs. Would definately stay again.

4.94 out of 5 average rating, 49 reviews

Farm stay in Rockport

Farmhouse Stables Barn Ste #1

KateRating, 5 stars1 week ago

Such a nice peaceful place to stay!Was welcomed with a box of delicious Parlor Doughnuts. Deb was super helpful and sweet! Enjoyed our stay!