Holiday rentals in Madisonville

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Top-rated holiday rentals in Madisonville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A cozy living room features two light-colored sofas adorned with blue and white patterned cushions. A round coffee table is positioned in the center, and a chess set is displayed on it. Soft blue walls complement the wooden dining area visible in the background.
Home in Madisonville
4.9 out of 5 average rating, 60 reviews

Roos&Blues lake house at the city park. Rm for 6

This home 🏡 offers a tranquil place next to the city park and view of lake. Home offers 2 large bedrooms both with king size beds. Each bedroom has their own heating and air with ozone cleaning to assist in the cleanest air we can provide. The living room offers a new queen sleeper sofa. Our kitchen is stocked many cooking appliances and pantry items but no stove or oven. Upon request we provide bikes, games, grills, memory foam top for sofa bed and most anything you need for infants/toddlers.

Guest favourite
Home in Madisonville
5 out of 5 average rating, 10 reviews

Peaceful Retreat

Close to downtown Madisonville, Kentucky Sports Factory/Sports Plex and one mile from Mahr park (walking trails, picnic pavilions, kayak launch,etc). Private backyard with patio, table/chairs and BBQ grill. Home has Smart TV w/ streaming channels, DVD player, WiFi, Keurig and drip coffee, toaster, pots, pans, cookie sheet, mixing bowls, etc. One queen bed, one king, single over full bunk and single day bed. Full size inflatable mattress upon request. Bedrooms are upstairs. No smoking. No pets.

Top guest favourite
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.
Home in Madisonville
4.99 out of 5 average rating, 101 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.

Guest favourite
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.
Home in Madisonville
4.96 out of 5 average rating, 28 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.

Guest favourite
A single-story home with a brick facade is presented. The driveway leads to a garage, while a well-maintained lawn features neatly trimmed grass and colorful flowerbeds. Large front windows allow for natural light, framed by light-colored siding underneath a gabled roof.
Home in Owensboro
4.94 out of 5 average rating, 135 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.

Top guest favourite
Cabin in Dixon
4.96 out of 5 average rating, 336 reviews

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.

Guest favourite
The treehouse is illuminated by soft outdoor lights, highlighting its wooden structure and welcoming design. A gently curving walkway leads to the entrance, surrounded by tall trees and a glimpse of Lake Malone visible in the background.
Treehouse in Lewisburg
4.95 out of 5 average rating, 156 reviews

Treehouse with HOT TUB!(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 hot tub, large deck, full kitchen, Jacuzzi tub, rainfall shower, beautiful woodwork, two complimentary kayaks, and many other unique features that will make your stay unforgettable.

Top guest favourite
Farm stay in Princeton
5 out of 5 average rating, 107 reviews

LUX Secret House & Adult Play Room

IF THIS LISTING IS BOOKED… find our Lux Secret Room #2 Grooms Suite! Luxury Guest House & Historical Gypsy horse farm and wedding venue with an adult theme room just a short drive from Nashville TN. Kentucky's finest example of a working horse farm woven into a magically designed wedding venue. Our herd of Gypsy horses is sure to capture your heart!!! Just 4 miles from I24 and close to dining and fun Patti’s 1880 Settlement! Perfect couple getaway for adults.

Top guest favourite
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.
Flat in Madisonville
5 out of 5 average rating, 98 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!

Top guest favourite
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
4.91 out of 5 average rating, 548 reviews

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.

Top guest favourite
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.
Farm stay in Hopkinsville
4.86 out of 5 average rating, 149 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.

Top guest favourite
A covered porch features wooden flooring and rustic decor. A bear-shaped welcome sign is positioned prominently, while a wooden storage chest stands against the wall. The space offers a view of lush greenery through the railing, enhancing the cabin's natural ambiance.
Home in Cadiz
4.95 out of 5 average rating, 147 reviews

* Charming 3 Bedroom Log Cabin On 4 Acres!

Welcome to Charming Cabin Lake Barkley State Resort Park Area! Cozy, local owner managed, remote cabin less than 5 minutes from Lake Barkley State Resort Park and close to Land Between the Lakes National Recreation Area. Beautiful wooded 4 acre lot with a huge covered deck and beautiful covered front porch nestled in the woods. Totally private & serene setting, w/ fire pit, gas grill, and plenty of nature.

Popular amenities for Madisonville holiday rentals

When is the best time to visit Madisonville?

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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Madisonville?

    Experience the best of Madisonville with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Madisonville?

    Yes! Work meets play with ease at over 30 vacation rentals in Madisonville featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Madisonville?

    Madisonville has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Madisonville?

    Four-legged friends are welcome in Madisonville. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Madisonville have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Madisonville. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Madisonville have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Madisonville. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Madisonville

  • Total holiday rentals

    Explore 70 holiday rentals in Madisonville

  • Nightly prices starting at

    Madisonville holiday rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 900 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Madisonville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Madisonville rentals

  • 4.9 Average rating

    Madisonville stays are highly rated by guests – averaging 4.9 out of 5!

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