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

Madison County Vacation Rentals

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Our top choices for Madison County vacation rentals

Living area

1. 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 CA $99
CA $227 total
includes taxes & fees
Sep 22 - Sep 23
Timberwolf Mobile Unit #2
Living area

2. 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 CA $174
CA $296 total
includes taxes & fees
Sep 17 - Sep 18
St Francis River: The Blue Yurt and Hot Tub
Terrace/patio

3. The Stonehouse - Private Hot Tub - Sleeps 5

The Stonehouse - Private Hot Tub - Sleeps 5
Fredericktown
9.8 out of 10, Exceptional, (7 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 price is CA $158
CA $288 total
includes taxes & fees
Sep 17 - Sep 18
The Stonehouse - Private Hot Tub - Sleeps 5
Interior

4. The Firehouse Loft - Sleeps 4

The Firehouse Loft - Sleeps 4
Fredericktown
8.0 out of 10, Very good, (1 review)
The price is CA $122
CA $261 total
includes taxes & fees
Sep 17 - Sep 18
The Firehouse Loft - Sleeps 4
Private kitchen

5. A-Frame - Hot Tub - Sleeps 7

A-Frame - Hot Tub - Sleeps 7
Fredericktown
The price is CA $216
CA $463 total
includes taxes & fees
Sep 17 - Sep 18
A-Frame - Hot Tub - Sleeps 7
Interior

6. 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
The price is CA $221
CA $331 total
includes taxes & fees
Sep 22 - Sep 23
RIVER and SKY Cabin; Hot Tub
Room

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 CA $199
CA $312 total
includes taxes & fees
Sep 18 - Sep 19
Conestoga Covered Wagon on Working Farm - Willowmere
Room

8. Conestoga Covered Wagon at Cherrywood Farms - Hearthstone

Conestoga Covered Wagon at Cherrywood Farms - Hearthstone
Fredericktown
The price is CA $192
CA $303 total
includes taxes & fees
Sep 18 - Sep 19
Conestoga Covered Wagon at Cherrywood Farms - Hearthstone
Pool

9. 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, (11 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 CA $243
CA $290 total
includes taxes & fees
Sep 17 - Sep 18
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
Living area

10. 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 CA $105
CA $238 total
includes taxes & fees
Sep 22 - Sep 23
Timberwolf Mobile Unit #1
Interior

11. Timberwolf Mobile Unit #3

Timberwolf Mobile Unit #3
Fredericktown
The price is CA $99
CA $241 total
includes taxes & fees
Sep 21 - Sep 22
Timberwolf Mobile Unit #3
Living area

12. Timberwolf Mobile Unit #4

Timberwolf Mobile Unit #4
Fredericktown
The price is CA $99
CA $241 total
includes taxes & fees
Sep 17 - Sep 18
Timberwolf Mobile Unit #4
Room

13. Conestoga Covered Wagon at Cherrywood Farm - Oakheart

Conestoga Covered Wagon at Cherrywood Farm - Oakheart
Fredericktown
The price is CA $202
CA $315 total
includes taxes & fees
Sep 17 - Sep 18
Conestoga Covered Wagon at Cherrywood Farm - Oakheart
Interior

14. The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.8 out of 10, Exceptional, (7 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 CA $105
CA $222 total
includes taxes & fees
Sep 19 - Sep 20
The Atrium - A Boutique Hotel
Interior

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

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (31 reviews)
"This is a very cozy, comfortable and quiet space. This cabin has everything you need and is close to restaurants and Elephant Rocks State Park. I would recommend to anyone visiting the area! Thank you!"
United States
Michelle
The price is CA $150
CA $248 total
includes taxes & fees
Sep 17 - Sep 18
Lake Road Cabin C — Million Dollar Ozark View!
Outdoor spa tub

16. Cozy 1-bedroom cabin in wonderful Leadwood with AC

Cozy 1-bedroom cabin in wonderful Leadwood with AC
Leadwood
10.0 out of 10, Exceptional, (4 reviews)
"The host was very helpful!"
United States
Lynn M.
The price is CA $63
CA $209 total
includes taxes & fees
Sep 20 - Sep 21
Cozy 1-bedroom cabin in wonderful Leadwood with AC
Private kitchen

17. "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, (28 reviews)
"Very nice stay we enjoyed would definitely stay again"
United States
Ben C.
The price is CA $168
CA $333 total
includes taxes & fees
Sep 17 - Sep 18
"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington
Living area

18. Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations

Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations
Farmington
9.2 out of 10, Wonderful, (9 reviews)
"Host was very helpful and accommodating! Very cute and small house, perfect for our weekend stay! "
United States
Amber P.
The price is CA $94
CA $206 total
includes taxes & fees
Sep 17 - Sep 18
Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations
Private kitchen

19. Cozy Three bedroom home in Central Farmington

Cozy Three bedroom home in Central Farmington
Farmington
9.8 out of 10, Exceptional, (35 reviews)
"Great little house and was perfect for our weekend trip to Farmington! Would recommend."
United States
Daniel K.
The price is CA $150
CA $354 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Three bedroom home in Central Farmington
Exterior

20. Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (289 reviews)
"The place was easy to find. Cute, clean, and relaxing. It was the perfect stay for our trip. Highly recommend. "
United States
Shayna P.
The price is CA $206
CA $277 total
includes taxes & fees
Sep 23 - Sep 24
Beautiful Modern Loft In Wine Country!
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 Madison County Hotel Reviews

Shepherd Mountain Inn

Shepherd Mountain Inn

10/10 Excellent
"ABSOLUTELY WONDERFUL STAY! We had a larger room that accommodated all 6 of us very easily. Breakfast was so great with something for everyone. Staff was helpful and provided anything we asked for."
Allison 2-night trip
Posted 6 hours ago
Shepherd Mountain Inn

Find out more about Madison County

Everything you need to know about Madison County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Madison County vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison County vacation rentals we have selected for you start as low as CA $204 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 vacation 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 vacation.

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.