A wooden pier extending into a calm body of water, surrounded by a forested shoreline under a cloudy sky.

Madisonville Holiday Rentals

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Our top choices for Madisonville holiday rentals

1. Union Station Union Station

Union Station Union Station
Madisonville
9.4 out of 10, Exceptional, (6 reviews)
"Was a beautiful house and a lovey stay! "
United States
Rhonda P.
The price is NZ$585
includes taxes & fees
4 Nov - 5 Nov
Union Station Union Station

2. Loop Haven is an awesome place to stay.

Loop Haven is an awesome place to stay.
Madisonville
9.4 out of 10, Exceptional, (14 reviews)
"Nice clean space with room for everything we needed. Host was quick to always keep us up to date on our reservation, check in and check out.One minor issue was resolved immediately. Would stay here again although it's not fenced in on one side so luckily that was not an issue for us."
United States
Dianne K.
Loop Haven is an awesome place to stay.

3. The Nisbet Nest The Nisbet Nest

The Nisbet Nest The Nisbet Nest
Madisonville
6.0 out of 10, (1 review)
The price is NZ$692
includes taxes & fees
17 Nov - 18 Nov
The Nisbet Nest The Nisbet Nest

4. Charming cabin with amazing views located on Toontucky Farms

Charming cabin with amazing views located on Toontucky Farms
White Plains
9.8 out of 10, Exceptional, (9 reviews)
" Stayed for a week very nice place. "
United States
Brandon L.
The price is NZ$293
includes taxes & fees
26 Oct - 27 Oct
Charming cabin with amazing views located on Toontucky Farms

5. Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby

Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby
Crofton
9.8 out of 10, Exceptional, (200 reviews)
"We had a great stay with our pup! Thanks for the lovely stay. We enjoyed the canoe."
United States
Patricia R.
The price is NZ$307
includes taxes & fees
28 Oct - 29 Oct
Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby

6. Beautiful Southern Home

Beautiful Southern Home
Sacramento
9.2 out of 10, Wonderful, (5 reviews)
"The host was accommodating, and the house was conveniently located near everything we needed it to be!"
United States
Courtney W.
The price is NZ$678
includes taxes & fees
26 Oct - 27 Oct
Beautiful Southern Home

7. Sweet Dreams in Sacramento

Sweet Dreams in Sacramento
Sacramento
8.4 out of 10, Very good, (6 reviews)
"This the second time that we have stayed at this location for the Civil War reenactment "
United States
Paul R.
The price is NZ$384
includes taxes & fees
26 Oct - 27 Oct
Sweet Dreams in Sacramento

8. Great for Family Reunions, Hunting Lodge And Pet Friendly!

Great for Family Reunions, Hunting Lodge And Pet Friendly!
Crofton
9.8 out of 10, Exceptional, (129 reviews)
"Great place with a lot of room. My youth group especially enjoyed the games downstairs"
United States
Andrew D.
The price is NZ$1,072
includes taxes & fees
26 Oct - 27 Oct
Great for Family Reunions, Hunting Lodge And Pet Friendly!

9. Quaint cottage with 3 queen beds and screened porch.

Quaint cottage with 3 queen beds and screened porch.
Crofton
10.0 out of 10, Exceptional, (96 reviews)
"Would definitely stay here again!"
United States
Becky S.
The price is NZ$538
includes taxes & fees
26 Oct - 27 Oct
Quaint cottage with 3 queen beds and screened porch.

10. Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.

Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.
Crofton
10.0 out of 10, Exceptional, (70 reviews)
"The cabin and location are beautiful, cozy, and so relaxing. It was so nice to be so close to the park for lake access and hiking, but to be able to return to the cabin to have a little retreat with privacy to make the weekend a really lovely getaway."
United States
Megan D.
The price is NZ$527
includes taxes & fees
26 Oct - 27 Oct
Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.

11. Cozy Nook Retreat - Fireplace /Full Kitchen

Cozy Nook Retreat - Fireplace /Full Kitchen
Crofton
8.8 out of 10, Excellent, (3 reviews)
"Check In was very easy, the host was pleasant and very responsive, and house was clean."
United States
Jessica W.
The price is NZ$381
includes taxes & fees
26 Oct - 27 Oct
Cozy Nook Retreat - Fireplace /Full Kitchen

12. Charming Treehouse with Lake View and Access

Charming Treehouse with Lake View and Access
Utica
9.8 out of 10, Exceptional, (124 reviews)
"Awesome place to have some time with family away from everyone."
United States
Lori
The price is NZ$267
includes taxes & fees
26 Oct - 27 Oct
Charming Treehouse with Lake View and Access

13. Enjoy mama’s House in a quiet little area of Crofton ky

Enjoy mama’s House in a quiet little area of Crofton ky
Crofton
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because my son got married at Burdoc Farms Oct 17th, 2026. The house was so cute, very clean and about 10 minutes from the venue. Any messages I sent to Phyllis, she got back to me promptly. The only downside was we would get back so late from setting up/wedding that it was too chilly to enjoy the front/back porch and gaze at all the stars. It’s just over a 2 hr drive (from Louisville) so if I needed a quick weekend reset, this would be the perfect quiet place to unwind."
United States
Shawn F.
The price is NZ$860
includes taxes & fees
26 Oct - 27 Oct
Enjoy mama’s House in a quiet little area of Crofton ky

14. Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space

Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space
Greenville
10.0 out of 10, Exceptional, (10 reviews)
"Awesome stay "
United States
Gregory S.
The price is NZ$601
includes taxes & fees
26 Oct - 27 Oct
Guitars & Harmony II in Historic Greenville with WiFi & beautiful outdoor space

15. Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro

Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
Utica
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful spot! The best "
United States
Andrea S.
The price is NZ$495
includes taxes & fees
12 Nov - 13 Nov
Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro

16. Lake Country House on City Square

Lake Country House on City Square
Princeton
9.8 out of 10, Exceptional, (29 reviews)
"Our stay was excellent and even better we were close to family so we didn't need to travel far after activities."
United States
Stacey S.
The price is NZ$499
includes taxes & fees
26 Oct - 27 Oct
Lake Country House on City Square
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madisonville Hotel Reviews

Find out more about Madisonville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madisonville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madisonville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Madisonville. Seeing all the best attractions is bound to make you fall in love with Madisonville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Madisonville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Madisonville?

Yes, there are holiday rentals in Madisonville close to Kentucky Sports Factory, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Madisonville has a good selection of restaurants. Make sure you have time to check out the monuments and golf courses during your trip.

What are some of the best holiday rentals that Madisonville has to offer?

Roos&Blues lake house. City park steps away. Rm for 6, king beds, pets friendly: This highly rated holiday home rental in Madisonville offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave. Our travellers also rate Union Station Union Station as a favourite home for rent in Madisonville.

How many holiday rentals will I find in Madisonville?

Expedia has 11 holiday rentals for your stay in Madisonville.

What’s there to see and do in Madisonville?

Madisonville City Park and Mahr Park are a couple of scenic spots to enjoy the outdoors, whereas Gleam Mahr Center for Arts is one of the cultural attractions. Other places in town to visit include Ruby Laffon Log Cabin and Madisonville Country Club.

What’s a holiday rental in Madisonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madisonville. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.