Photo by Morgan O'riley

Madison County Vacation 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

Top cities in Madison County

A clear stream with large rocks and trees in a forested area.
Vacation Rentals

Fredericktown

Fredericktown

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Madison County vacation rentals

A modern interior with a sofa, a washing machine, and a view through a glass door.

1. Timberwolf Mobile Unit #3

Timberwolf Mobile Unit #3
Fredericktown
The price is CA $108
CA $235 total
includes taxes & fees
Nov 29 - Nov 30
Timberwolf Mobile Unit #3
A wooden deck with outdoor seating and a fire pit, surrounded by trees.

2. 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 price is CA $135
CA $247 total
includes taxes & fees
Nov 22 - Nov 23
The Stonehouse - Private Hot Tub - Sleeps 5
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, (28 reviews)
"Loved it would stay again "
United States
Ashley B.
The price is CA $175
CA $286 total
includes taxes & fees
Nov 8 - Nov 9
St Francis River: The Blue Yurt and Hot Tub
A compact bathroom with a shower, toilet, and a small sink area.

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 $166
CA $294 total
includes taxes & fees
Nov 11 - Nov 12
The Firehouse Loft - Sleeps 4
A modern room with a large window, two chairs, a small wooden table, and a view of a forest.

5. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.2 out of 10, Wonderful, (7 reviews)
"Lpleasant environment, beautiful view, the cabin was super clean and enjoyableonly note being the bed was stiff and pillows were thin but overall would recommend"
United States
Teresa C.
The price is CA $223
CA $338 total
includes taxes & fees
Nov 10 - Nov 11
RIVER and SKY Cabin; Hot Tub
A circular stone fire pit surrounded by grass and trees in a natural setting.

6. Hearthstone Covered Wagon - Pond + Farm View, Wagon Glamping, Fire Pit

Hearthstone Covered Wagon - Pond + Farm View, Wagon Glamping, Fire Pit
Fredericktown
10.0 out of 10, Exceptional, (3 reviews)
"Had a very nice stay. Went to Fredericktown for my class reunion and stayed in the wagons. The reunion was at the golf course and this was very nice to stay in the wagon on site. There was a problem with the room and I contacted the owner and was moved to another wagon next site. We enjoyed the fire and sitting and relaxing before went to bed. Bed was very comfortable. Host was awesome a d check in and check out was very smooth."
United States
sheila k.
The price is CA $209
CA $304 total
includes taxes & fees
Nov 13 - Nov 14
Hearthstone Covered Wagon - Pond + Farm View, Wagon Glamping, Fire Pit
A bathroom with a wooden vanity, a hanging basket, and a window with curtains.

7. Willowmere Covered Wagon - Pond View, Glamping Getaway, Farm, & Fire Pit

Willowmere Covered Wagon - Pond View, Glamping Getaway, Farm, & Fire Pit
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 $216
CA $311 total
includes taxes & fees
Nov 13 - Nov 14
Willowmere Covered Wagon - Pond View, Glamping Getaway, Farm, & Fire Pit
A hot tub in a covered outdoor area with a view of a swimming pool and a wooden play structure in the background.

8. 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, (15 reviews)
"Host was very kind and every thing we needed was right there . We was to bust with out trip to enjoy the cooking out spot . Highly recommend"
United States
hannah
The price is CA $245
CA $273 total
includes taxes & fees
Nov 8 - Nov 9
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
A narrow hallway with a loft bedroom above, a ladder, and a small window.

9. Authentic Train Caboose with Loft & Firepit Near Elephant Rocks

Authentic Train Caboose with Loft & Firepit Near Elephant Rocks
Fredericktown
10.0 out of 10, Exceptional, (4 reviews)
"Our stay was perfect. Tina was a great host, and the caboose was absolutely perfect in every way. The muffins were great. Will definitely plan another visit to this wonderful getaway. Thank you"
United States
Bob A.
The price is CA $337
CA $372 total
includes taxes & fees
Nov 17 - Nov 18
Authentic Train Caboose with Loft & Firepit Near Elephant Rocks
A compact, modern RV interior with a kitchenette, a sofa, and a staircase leading to an upper level.

10. 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 $135
CA $271 total
includes taxes & fees
Nov 9 - Nov 10
Timberwolf Mobile Unit #2
A modern interior with a sofa, a kitchen area, and large windows.

11. Timberwolf Mobile Unit #4

Timberwolf Mobile Unit #4
Fredericktown
The price is CA $135
CA $274 total
includes taxes & fees
Nov 15 - Nov 16
Timberwolf Mobile Unit #4
A modern RV interior with a sofa, a kitchenette, and large windows.

12. 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 $135
CA $274 total
includes taxes & fees
Nov 29 - Nov 30
Timberwolf Mobile Unit #1
A bathroom with a wooden vanity, a hanging basket, and a window with curtains.

13. Oakheart Covered Wagon - Farm Life, Pond View Glamping, Fire Pit, River

Oakheart Covered Wagon - Farm Life, Pond View Glamping, Fire Pit, River
Fredericktown
The price is CA $250
CA $345 total
includes taxes & fees
Nov 15 - Nov 16
Oakheart Covered Wagon - Farm Life, Pond View Glamping, Fire Pit, River
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
9.4 out of 10, Exceptional, (12 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 $124
CA $142 total
includes taxes & fees
Nov 8 - Nov 9
The Atrium - A Boutique Hotel
A wooden deck structure with a red exterior and string lights, a car parked nearby, and a tree in the foreground.

15. Cozy hobby farm cabin under the stars with treehouse, & hot tub

Cozy hobby farm cabin under the stars with treehouse, & hot tub
Patterson
9.6 out of 10, Exceptional, (12 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is CA $111
CA $164 total
includes taxes & fees
Nov 9 - Nov 10
Cozy hobby farm cabin under the stars with treehouse, & hot tub
A wooden dining table with two wine glasses and a basket containing a bottle of champagne, snacks, and a bottle of Welch's.

16. Cozy 1-bedroom house with AC and WiFi in charming Farmington

Cozy 1-bedroom house with AC and WiFi in charming Farmington
Farmington
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful and perfect for travelers!!!!!"
United States
Elizabeth
The price is CA $119
CA $261 total
includes taxes & fees
Dec 2 - Dec 3
Cozy 1-bedroom house with AC and WiFi in charming Farmington
A compact living space with a sofa, dining table, kitchen area, and a ceiling fan.

17. 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
9.4 out of 10, Exceptional, (11 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 $100
CA $202 total
includes taxes & fees
Nov 9 - Nov 10
Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations
A kitchen with wooden cabinets, a toaster, and a dishwasher.

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

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (34 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
The price is CA $151
CA $241 total
includes taxes & fees
Nov 10 - Nov 11
Lake Road Cabin C — Million Dollar Ozark View!
A cabin interior with a loft bed, a chair, and a ceiling fan.

19. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (66 reviews)
"great place to get away. plan to cook/grill there, or drive 30 minutes for food. however, this solitude and quiet is exactly why we booked here. and gorgeous roads, hikes, sites in every direction."
United States
Hans S.
The price is CA $170
CA $290 total
includes taxes & fees
Nov 8 - Nov 9
Hillside Cabin #2 Annapolis, MO Black River
A compact kitchen with wooden cabinets, a large TV, and various kitchen utensils hanging on the wall.

20. FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.2 out of 10, Wonderful, (11 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is CA $153
CA $277 total
includes taxes & fees
Nov 8 - Nov 9
FS Rental #4 Annapolis, MO Black River
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

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Madison County Hotel Reviews

A hotel lobby with a reception desk, seating area, and a patterned carpet.
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG
Perryville

10/10 Excellent

Great Place to Stay! Customer so friendly and nice there!
Canada
Shavanie
Reviewed March 3, 2025
Holiday Inn Express & Suites Perryville by IHG

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 $123 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.