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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Superhost
A single-level home is featured with a welcoming front porch swing, framed by greenery. The entrance includes a ramp, allowing for easy access. The yard includes a pathway that leads to the front door, enhancing the welcoming atmosphere of the residence.
Home in Sacramento
4.73 out of 5 average rating, 15 reviews

CROSSROADS COTTAGE

This home welcomes you with a front porch swing and a small side deck to visit with family and friends; the side has a ramp entrance. WIFI and TV are included. Nice size kitchen and livingroom for relaxing and visiting. The office has a daybed with trundle - great for children and teens. Churches, restaurants, bank, and post office are in walking distance. Grocery, Dollar General, hair/nail salon & fashion, gas stations, auto mechanic shops, hardware, and funeral home are within one mile.

Guest favourite
An inviting living area features a brown leather sofa, accent pillows, and a round coffee table. A modern ceiling fan is positioned above, while large windows are adorned with light curtains. A decorative mirror and seasonal decor enhance the warmth of the space.
Home in Madisonville
4.8 out of 5 average rating, 5 reviews

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.

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
4.95 out of 5 average rating, 19 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.

Top guest favourite
Cabin in Dixon
4.96 out of 5 average rating, 322 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.

Top guest favourite
The cabin is nestled among tall trees, showcasing a rustic wooden exterior. Soft lights glow from the windows, hinting at warmth inside. A gravel driveway leads to the front porch, where welcoming seating is arranged, complemented by the vibrant hues of a sunset sky.
Cabin in Madisonville
4.98 out of 5 average rating, 81 reviews

My Old Kentucky Home Log Cabin Private Retreat

Go back in time for awhile! Enjoy this vintage 3 bedroom cabin with the old thyme feel but with the modern conveniences needed. Private, quiet, cozy and relaxing, it makes the perfect family getaway. Enjoy your morning coffee on the front deck and hot chocolate by the fireside. Take a walk around the property and have a hamburger fry/ hot dog roast by a lively fire. Enjoy a week renewing your family connections, romantic getaway or simply have a grand time with your friends!

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, 83 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, 529 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
4.85 out of 5 average rating, 142 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.

Guest favourite
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
4.94 out of 5 average rating, 298 reviews

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.

Guest favourite
A cozy living area is furnished with two comfortable recliners and a square coffee table. Light-colored decor elements adorn the wall, while natural light enters through a window with soft coverings. A patterned rug complements the warm wooden flooring.
Home in Madisonville
5 out of 5 average rating, 97 reviews

Four-Fifty on Stagecoach

Have fun with the whole family at this newly furnished and stylish place. This cozy home is Located in a quiet & safe rural area north of Madisonville. If you need additional space or have interest in a second property check out our Whippoorwill Farmhouse located just up the road.

Top guest favourite
A charming farmhouse with a white exterior and dark shutters is presented. The inviting porch features a warm light, flanked by two trees, creating a cozy ambiance. A gravel pathway leads toward the entrance, set within a green lawn that offers a tranquil environment.
Home in Slaughters
5 out of 5 average rating, 14 reviews

Shady Maple Farm

Step into the charm of yesteryear at our beautifully updated 1910 farmhouse, nestled in the heart of Kentucky’s rolling hills. This peaceful retreat offers a serene escape from the hustle and bustle of city life, surrounded by pastures, wooded areas and scenic farmland.

Superhost
A spacious kitchen area features a granite countertop with three metal stools. A refrigerator and stove are visible, along with various kitchen appliances. The room is accented by exposed brick, and light from a window brightens the space.
Flat in Madisonville
5 out of 5 average rating, 3 reviews

Darwin's Condo

Take it easy at this unique and tranquil getaway. This is an upstairs unit (note stairs). This unit has been attractive to medical students. Full kitchen and washer dryer with Wi-Fi and streaming tv and all utilities make this unit an exceptional value.

Popular amenities for Madisonville holiday rentals

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Frequently Asked Questions

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

    Experience the best of Madisonville with our apartment 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 house rentals in Madisonville have wifi?

    Absolutely! We offer over 30 house 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 60 holiday rentals in Madisonville

  • Nightly prices starting at

    Madisonville holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 820 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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