A rocky trail surrounded by large boulders and leaf-covered ground.

Madison County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Madison County holiday rentals

A modern kitchen with a wooden ceiling, a black refrigerator, a sink, bar stools, and a large window.

1. A-Frame - Hot Tub - Sleeps 7

A-Frame - Hot Tub - Sleeps 7
Fredericktown
The price is NZ$662
includes taxes & fees
26 Oct - 27 Oct
A-Frame - Hot Tub - Sleeps 7
A hot tub in a covered outdoor area with a view of a swimming pool and a wooden play structure in the background.

2. Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
Fredericktown
10.0 out of 10, Exceptional, (13 reviews)
"This was one of the best stays we have ever had! The owners Cathy and Richard are absolutely incredible! They go above and beyond to make sure you have the best time possible! The amities are just non stop! I 100% recommend and will definitely be back!"
United States
Lexis
The price is NZ$368
includes taxes & fees
8 Oct - 9 Oct
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
A cozy interior with a leather sofa, a flat-screen TV, and a wooden table.

3. St Francis River: The Blue Yurt and Hot Tub

St Francis River: The Blue Yurt and Hot Tub
Fredericktown
8.8 out of 10, Excellent, (27 reviews)
"Loved it would stay again "
United States
Ashley B.
The price is NZ$377
includes taxes & fees
12 Oct - 13 Oct
St Francis River: The Blue Yurt and Hot Tub
A modern room with a large window, two chairs, a small wooden table, and a view of a forest.

4. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.4 out of 10, Exceptional, (6 reviews)
"Great getaway"
United States
Anonymous traveller
RIVER and SKY Cabin; Hot Tub
A compact, modern RV interior with a kitchenette, a sofa, and a staircase leading to an upper level.

5. Timberwolf Mobile Unit #2

Timberwolf Mobile Unit #2
Fredericktown
10.0 out of 10, Exceptional, (1 review)
"The stay was amazing. Property was beautiful."
United States
Connor B.
The price is NZ$344
includes taxes & fees
8 Oct - 9 Oct
Timberwolf Mobile Unit #2
A wooden deck with outdoor seating and a fire pit, surrounded by trees.

6. The Stonehouse - Private Hot Tub - Sleeps 5

The Stonehouse - Private Hot Tub - Sleeps 5
Fredericktown
9.8 out of 10, Exceptional, (8 reviews)
"The Stonehouse was every bit as cute and comfortable as expected! We enjoyed staying here as a great base for hiking in the area. The tiny town is a neat complex of different types of place to stay plus the Station coffee house was great to have in walking distance. "
United States
Beth A.
The Stonehouse - Private Hot Tub - Sleeps 5
A cozy, circular room with a bed, a wooden table, and a small window.

7. Conestoga Covered Wagon on Working Farm - Willowmere

Conestoga Covered Wagon on Working Farm - Willowmere
Fredericktown
10.0 out of 10, Exceptional, (1 review)
"My stay here was amazing! All the staff were very kind. I was the only one staying there at the time and everyone was very friendly. When they say that you're staying on a working farm that's exactly what they mean that that's what made it. Such a cool experience. Staying inside a covered wagon that had modern amenities was a cool experience. It kept cool inside with the air-conditioning. The bed was extremely comfortable. There was coffee available for me every morning, which is a plus for me...
United States
Karen S.
The price is NZ$394
includes taxes & fees
9 Oct - 10 Oct
Conestoga Covered Wagon on Working Farm - Willowmere
A cozy, circular room with a bunk bed, a small table with a chair, and a television.

8. Conestoga Covered Wagon at Cherrywood Farms - Hearthstone

Conestoga Covered Wagon at Cherrywood Farms - Hearthstone
Fredericktown
10.0 out of 10, Exceptional, (1 review)
The price is NZ$436
includes taxes & fees
20 Oct - 21 Oct
Conestoga Covered Wagon at Cherrywood Farms - Hearthstone
A compact bathroom with a shower, toilet, and a small sink area.

9. The Firehouse Loft - Sleeps 4

The Firehouse Loft - Sleeps 4
Fredericktown
8.0 out of 10, Very good, (1 review)
The price is NZ$379
includes taxes & fees
8 Oct - 9 Oct
The Firehouse Loft - Sleeps 4
A cozy, circular room with a bed, a wooden table, and a small window.

10. Conestoga Covered Wagon at Cherrywood Farm - Oakheart

Conestoga Covered Wagon at Cherrywood Farm - Oakheart
Fredericktown
The price is NZ$445
includes taxes & fees
11 Oct - 12 Oct
Conestoga Covered Wagon at Cherrywood Farm - Oakheart
A modern RV interior with a sofa, a kitchenette, and large windows.

11. Timberwolf Mobile Unit #1

Timberwolf Mobile Unit #1
Fredericktown
8.0 out of 10, Very good, (1 review)
"It was a pleasure to stay there"
United States
Brad W.
The price is NZ$369
includes taxes & fees
14 Oct - 15 Oct
Timberwolf Mobile Unit #1
A modern interior with a sofa, a washing machine, and a view through a glass door.

12. Timberwolf Mobile Unit #3

Timberwolf Mobile Unit #3
Fredericktown
The price is NZ$318
includes taxes & fees
20 Oct - 21 Oct
Timberwolf Mobile Unit #3
A modern interior with a sofa, a kitchen area, and large windows.

13. Timberwolf Mobile Unit #4

Timberwolf Mobile Unit #4
Fredericktown
The price is NZ$344
includes taxes & fees
20 Oct - 21 Oct
Timberwolf Mobile Unit #4
A rustic interior with exposed brick walls, wooden railings, and a hanging floral chandelier.

14. The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.8 out of 10, Exceptional, (8 reviews)
"What an amazing little suite wrapped in a very thought-filled overall venue. Very unique room with a so many details. The overall building with fire pit, game rooms, and local vendor items…all was quite amazing. Every element is thought out very well. It is very convenient and overall comfortable. It was a great getaway."
United States
Brian
The price is NZ$284
includes taxes & fees
8 Oct - 9 Oct
The Atrium - A Boutique Hotel
A modern kitchen with a large island, stainless steel appliances, and exposed brick walls.

15. Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful place and staff was amazing!"
United States
Grace
The price is NZ$553
includes taxes & fees
9 Oct - 10 Oct
Urban Lofts
A rustic log cabin with a stone foundation, surrounded by trees and a wooden fence.

16. Sam A Baker State Park

Sam A Baker State Park
2.0 star property
Patterson
9.0 out of 10, Wonderful, (6 reviews)
"Pet friendly, great staff. "
United States
Charlie
The price is NZ$254
includes taxes & fees
18 Oct - 19 Oct
Sam A Baker State Park
A wooden deck with a table and chairs, a window, and a view of trees.

17. Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Ste. Genevieve
10.0 out of 10, Exceptional, (63 reviews)
"Very charming log cabin perfect for a girls’ weekend close to the winery very clean property easy to reach the host. This is my third stay here and I would definitely stay again."
United States
Cheryl B.
The price is NZ$667
includes taxes & fees
8 Oct - 9 Oct
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
A modern kitchen with grey cabinets, a black refrigerator, and a microwave.

18. "The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington

"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington
Farmington
10.0 out of 10, Exceptional, (30 reviews)
"Very nice stay we enjoyed would definitely stay again"
United States
Ben C.
The price is NZ$417
includes taxes & fees
30 Oct - 31 Oct
"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington
A kitchen with wooden cabinets, a toaster, and a dishwasher.

19. Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (32 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
The price is NZ$318
includes taxes & fees
8 Oct - 9 Oct
Lake Road Cabin C — Million Dollar Ozark View!
A porch with four green Adirondack chairs, a small table, and string lights.

20. *State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (41 reviews)
"Great place to stay!"
United States
Derek R.
The price is NZ$521
includes taxes & fees
8 Oct - 9 Oct
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison County Hotel Reviews

Crown Pointe Lodge, BW Signature Collection

Crown Pointe Lodge, BW Signature Collection

8/10 Good
"Wife loved the breakfast but couldn't use a remodel"
Rebekah 1-night trip
Posted 1 day ago
Crown Pointe Lodge, BW Signature Collection

Find out more about Madison County

Everything you need to know about Madison County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madison County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Madison County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison County holiday rentals we have selected for you start as low as NZ$215 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madison County rentals

At Expedia, we put the best Madison County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Madison County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.