Vacation rentals in Madisonville

A cozy living area is presented with a comfortable seating arrangement, featuring a light grey armchair and a patterned upholstered sofa. A flat-screen TV is positioned on a stylish console, and large windows allow natural light to illuminate the space, offering views of the outdoor setting.

4.99 out of 5 average rating, 73 reviews

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.

Superhost

A charming house from 1884 with a covered front porch supported by white columns. The exterior features a combination of green siding and orange accents. Lush grass surrounds the home, contributing to a welcoming outdoor space.

4.88 out of 5 average rating, 8 reviews

Late 1800's home - spacious and updated

Located close to everything in Madisonville and a short walk to downtown. 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.

4.89 out of 5 average rating, 28 reviews

A cozy cabin stands surrounded by a well-maintained lawn, with three large windows adorning its bright red exterior. Lush greenery frames the structure, while a screened-in porch is visible, providing a serene view of the landscape. Tall trees offer shade nearby.

Cabin in Calhoun

Little Red on the Green River

Little Red on the Green is the perfect getaway if you enjoy the peacefulness of watching the river flow downstream. This simple, cute, cozy, 600 square foot, one room cabin is sure to be enjoyed. The private riverfront, property is just steps from the river bank. If you like to fish, this might be the perfect spot! If you have a boat, the Calhoun boat ramp is only 2 miles away. This property is centrally located - 25 miles north-east of Madisonville, 20 miles south of Owensboro, Ky.

4.96 out of 5 average rating, 302 reviews

A serene lakeside view captures a quaint cabin reflected in calm waters. Lush green grass surrounds the water's edge, while trees frame the background under a blue sky dotted with clouds.

Cabin in Dixon

Crouse’s North Ninety Lake House

If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

Apartment in Madisonville

A modern duplex with a crisp white exterior is presented, featuring a dark roof and large windows. Two front doors, one for each unit, are framed by charming landscaping. Surrounding trees display vibrant autumn foliage, enhancing the inviting outdoor space.

5 out of 5 average rating, 68 reviews

Modern, Quiet, Hidden Gem: Manna House (5)

Kick back and relax in this peaceful, brand new, stylish space. Located close to town yet feels like a hidden country paradise. This unit is one of two units available at a duplex situated on 5 acres. With 10 foot ceilings this one bedroom feels so much bigger! It offers a walk in tile shower, King bed and Queen sleeper sofa, full kitchen with Quartz countertops, KitchenAid appliances, and includes full size stacked washer/dryer. We think you will love it here!

4.9 out of 5 average rating, 511 reviews

The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.

Cabin in Dixon

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

Farm stay in Hopkinsville

The kitchen features a U-shaped countertop with wooden cabinetry and a deep sink, complemented by a tile backsplash. A dining area with a round table and chairs is visible in the background, along with a decorative wall piece and clock adding subtle detail to the space.

4.85 out of 5 average rating, 131 reviews

Quiet country setting.

Hello! Thank you for considering staying with us during your stay in or around Hopkinsville, Ky. Whether you’re coming for work, pleasure or, to visit family, we think you’ll love staying here. It’s a warm and inviting home, with all the amenities you need for the perfect stay. We live on the farm, and will be around if you require anything during your stay. Please email if you have any questions. We look forward to hearing from you.

4.88 out of 5 average rating, 32 reviews

A charming farmhouse is displayed surrounded by trees, providing a tranquil outdoor setting. The exterior features a light-colored façade with dark shutters and two entrance staircases. A patio table and chairs are visible on the gravel area, enhancing the inviting outdoor space.

Home in Bremen

The Tumbling K

This lovely farmhouse is the perfect place for a weekend getaway or a business trip. Wake up to beautiful blue skies and the birds singing. If you need to stay connected, Wi-Fi is available. If you want to disconnect, you can enjoy a book with your favorite cup of coffee in a quiet setting. Perfectly located between Madisonville, KY & Central City, KY. 62 miles from Evansville, IN 97 miles from Nashville, TN

Tiny home in Hopkinsville

A spacious bedroom features large glass doors, offering views of the surrounding nature. Soft natural light fills the room, highlighting a comfortable queen bed with crisp linens. Nearby, a cozy seating area and a small workspace complement the inviting atmosphere.

5 out of 5 average rating, 138 reviews

Romantic, Peaceful Getaway in Nature

Enjoy beautiful views of nature when you stay in this unique place! Large windows on two sides of the home make it a truly serene space. Whether you are looking to walk trails on the property or enjoy the scenery in the comfort of home, you will find serenity during your stay here. If you'd like to bring a well-behaved dog, check out our other very similar rental! www.airbnb.com/h/3907witty

4.97 out of 5 average rating, 116 reviews

The two-story home, identified as River Trails Inn, features a welcoming facade with a front porch and American flag. Lush green grass surrounds the property, and a clear blue sky provides a serene backdrop. Well-maintained landscaping enhances the inviting appearance of the entrance.

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!!

4.94 out of 5 average rating, 269 reviews

The cabin features a welcoming front porch with wooden railings and steps leading up to a central door with a rustic design. Natural wood elements complement the structure, blending with the surrounding greenery for an inviting appearance.

Cabin in Hopkinsville

1 Bedroom, 1 Bathroom Cozy Cabin with Hot Tub.

The Lodge is a small 2 person only cabin on 45 acres of western KY countryside with amazing sunsets included. It has a private drive and a relaxing front porch with a 2 person only hot tub. Once you walk through the cabin doors, you will be transported to the Smokey mountains without the mountains. The owners live onsite if any problems arise that need immediate attention.

Superhost

This spacious bedroom features a large bed adorned with a teal coverlet. Decorative dark wood furniture is positioned around the room, including nightstands with lamps and a prominent mirror. An arched window allows natural light to fill the space, enhancing the serene atmosphere.

4.95 out of 5 average rating, 21 reviews

Church Becomes Your Temporary Home

COMPLETELY NON-SMOKING INSIDE AND OUTSIDE property is a beautifully re-imagined church great open loft style commercial heating and air two blocks from downtown bright and comfortable amazing large bathroom with glassed shower and teal soaking tub all wood and tile flooring - no nasty carpets

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

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Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Madisonville places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Madisonville

A serene landscape is captured during twilight, showcasing a barn structure set against a vibrant pink and purple sky. Silhouetted trees outline the scene, while a grassy area leads towards the building, evoking the tranquil beauty of the countryside.

Home in Dawson Springs

5 out of 5 average rating, 3 reviews

Kentucky Modern Farmhouse

5 out of 5 average rating, 50 reviews

A stunning sunset paints the sky in vibrant oranges and purples, viewed from a gravel parking area. The silhouettes of vehicles are visible in the foreground, while rolling fields and tree lines frame the horizon.

Barn in Hopkinsville

Barn Loft with Panoramic View

A charming house is presented with green siding and brick accents, framed by neatly trimmed shrubs. Two steps lead up to a covered porch, where a decorative front door is flanked by windows, providing a welcoming entryway under the soft evening sky.

4.9 out of 5 average rating, 50 reviews

Downtown Charm — walk anywhere!

Shipping container in Eddyville

A shipping container tiny home is shown, with a wooden deck extending from the entrance. The exterior features weathered metal siding and a simple design. Lush green grass surrounds the structure, with trees providing natural shade nearby.

4.93 out of 5 average rating, 74 reviews

Woodland Trails

5 out of 5 average rating, 69 reviews

A serene view of Lake Beshear is showcased, revealing the gentle curves of the shoreline and lush greenery. The landscape features a blend of trees and open water, with distant homes visible on the opposite bank under a clear blue sky.

Home in Dawson Springs

Quiet Lake House with Awesome View.

Camper/RV in Princeton

5 out of 5 average rating, 3 reviews

Cozy Farm Hideaway