Vacation rentals with a patio in Madisonville

Whippoorwill Farmhouse

Relax with the whole family at this peaceful place to stay. Located just two miles from the city, this fourth generation 1933 farmhouse has been recently remodeled inside and out. Enjoy relaxing in the enclosed front porch or the wrap around deck with views of the 180-acre working crop farm. Guests can enjoy a nice stroll around the farm, drop a line in the stocked pond, and spend time around the fire talking and roasting smore's. Ask your host about group events and hayrides around the farm.

Cozy 2 Bedroom House

Step inside our cozy, open concept, 2 bedroom home with ample kitchen space. The open kitchen is equipped with high-end appliances and a central island, perfect for preparing delectable meals. We make sure you have everything a cooking enthusiasts may need. Enjoy the weather, while grilling in the large backyard. We offer a variety of games for the whole family to enjoy. If you forget toiletries, we make sure you're covered with extras. Pickle ball court and kids area within walking distance.

The Nest - Huge Loft in Downtown Henderson

Welcome to The Nest, Henderson's finest loft! This Victorian 1800 sq. ft. loft is newly renovated, fully furnished and nicely appointed in the heart of Downtown Henderson. The huge living room is perfect to meet friends, watch TV, cook, or just gaze out the massive windows. The Master Room, Reading Room (featuring a queen Murphy bed), fully equipped Kitchen, and Private Patio are quiet spaces to relax, work, prepare a meal, or plan your day. Parking, fast wifi, and washer/dryer all included!

4bed3BR 30 to HolidayWorld/Near Conv Ctr/Fisher Pk

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv! Home is 3 miles from Convention Ctr, Bluegrass Museum, Science Museum, Botanical Garden. It’s also 4 minutes from baseball fields (Fischer), Thompson Berry( soccer), 30 min to Holiday world, private and fenced backyard with lighted patio. Home is well stocked with ALL you may need! If the home is empty previous night, early check in, no charge! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen, book now!

Cozy Cabin with Private Walking Trail

Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

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.

The FunKY Bean

Take it easy at this unique and tranquil getaway on beautiful Lake Malone. Relax in a hammock, swim off the dock , kayak , stand up paddle board, fish, or enjoy a beautiful sunrise while drinking your specialty coffee or tea! With the bean theme: There are oversized bean bags to relax on and a coffee station with LOTS of coffee options ( including Esspresso maker)! Outside you will have a solo fire pit ( wood not included - so grab a bundle on the way in ) and a gas grill .

3 bedroom, close to downtown & KY sports factory

Located close to everything in Madisonville. Only about a 5 minute drive to most parks, hospitals and all the local spots downtown. Minutes from the Kentucky Sports Factory and Elmer Kelly Stadium. 25-30 minutes to Dawson Springs and the beautiful scenery at Pennyrile State Park. Ideal for traveling nurses, co ops at local factories or those traveling for family events, wedding weekends, and visiting friends. Smoking and vaping on the property is not allowed

The Geneva Cabin

The Geneva Cabin is one of a kind (not in the woods) and has everything you need to enjoy whatever occasion brings you to the area. Located less than 2 miles from the wildlife refuge, 10 min to downtown Henderson, 7 mi to I-69 the property sits in the middle of a quiet dead-end street. Right in the middle of anywhere anyway your journey takes you. 55” TV, sofa bed and recliner in living room, WIFI, washer & dryer. Fully equipped kitchen. Large parking area.

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Come relax in our brand new Amish-made mini-HIDEAWAY! (Couples, friends, mother/daughter, business, or ME-time). We built our DREAM PLACE (with a brand new hot tub, GAS grill, and GAS firepit), and we are now sharing it with you! Located on 20 acres in the beautiful hills of Kentucky, you will be AMAZED at the sunsets and quietness. There are no near neighbors except the chirping birds and our horses to pet, watch, and feed. Come be refreshed!

Loop Haven

Welcome to our delightful three-bedroom house, nestled in the heart of a quaint small town. Perfect for a relaxing getaway, this home offers all the comforts you need for a peaceful and enjoyable stay. The interior is warm and inviting, featuring a comfortable living room where you can unwind after a day of exploring. Local shops, cafes, and parks are just a short drive away, offering plenty of opportunities to explore and enjoy the area.

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. 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.