Holiday rentals in Fredericktown

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Top-rated holiday rentals in Fredericktown

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Top guest favourite
A vibrant red barn with an American flag motif is featured alongside a well-maintained gravel path. The barn displays a sign quoting a biblical verse, and a historic farmhouse is visible in the background against a clear blue sky.
Farm stay in Frohna
4.98 out of 5 average rating, 129 reviews

The Weber Farm - Enjoy a beautiful 100 acre farm!

Enjoy a 125+ year old country home with large yard and beautiful shade trees located on a 100-acre farm in the rolling hills of SE Missouri. The house is very clean and spacious with 4 large bedrooms, comfortable beds, beautiful hardwood floors and a large living room. We have hand-made quilts and antique furniture throughout. The kitchen is fully furnished. Relax on our 40’ front porch with swing, by the fire pit or in a hammock. A perfect place for you to recharge from stress & busy schedules!

Top guest favourite
The geodesic dome is positioned among tall trees, illuminated by the glow of a fire pit in the foreground. A staircase leads up to the entrance, under a darkening sky with early stars becoming visible.
Dome in Perryville
4.94 out of 5 average rating, 164 reviews

The Snow Globe*OffGrid DomeGLAMP*Adventurers Only

EXPERIENCE The Dome in the Woods • IMMERSE in complete silence with the absence of electricity: no hum or vibrations from this completely solar/propane fueled geodesic dome. NoAC • GLAMP in this OFF GRID ADVENTURE. 430 sq ft floor plan. 14 ft ceiling. 20 ft bay window with endless nature view at the foot of your bed. Lofted 7ft. • STARGAZE from the deck or fire pit • NESTLE in the romantic wooded nature of southeast MO. S of St Louis.N of Memphis • UNPLUG, UNWIND, RELAX. Adventure seekers only!

Guest favourite
An aerial view captures the carriage house with a spacious deck and an umbrella-covered table, complemented by decorative shrubs lining the property. The driveway accommodates multiple vehicles, while a flag adds a touch of charm to the inviting exterior.
Home in Farmington
4.98 out of 5 average rating, 122 reviews

Columbia Street Carriage House

Located in historic downtown Farmington, minutes away from restaurants, wineries, shops, and parks. Our newly renovated carriage house has much to offer! Our 2+ acre yard is fully fenced with a gated entrance offering privacy, a fire pit, covered patio, and large deck. The city park is located next door with a private acces gate offering basketball courts, pickle ball, tennis, swing sets, pavilions and playgrounds. Come enjoy a relaxing weekend or stay a week exploring the area attractions.

Guest favourite
A lakeside view showcases calm waters reflecting morning light. The home’s exterior features gray siding and white shutters. A grassy lawn is observed, bordered by a large tree. The scene captures the peaceful surroundings, inviting guests to experience the tranquil setting.
Home in Fredericktown
4.93 out of 5 average rating, 135 reviews

The GooseNest • HOT TUB • Lake View

Enjoy a comfortable stay at this unique lakeside retreat. This home offers two bedrooms and one bathroom. Start your day with coffee and a view of the lake. You’ll stay a short drive from surrounding sites, including Millstream Gardens Conservation Area, Castor River Shut-ins, Elephant Rocks State Park, Johnson Shut-Ins State Park, Marble Creek Recreation Area, and Taum Sauk Mountain. Bring your fishing pole and kayak! End your day relaxing by the fire pit and watching the sunset on the lake

Top guest favourite
A light-colored farmhouse is presented with a prominent stone chimney, featuring a welcoming front porch with wooden railings. Lush greenery, including a trimmed bush, enhances the entryway. Gravel leads up to the house, surrounded by open space and trees in the background.
Farm stay in Fredericktown
4.95 out of 5 average rating, 191 reviews

Spring Valley Ranch Rock House

This quaint farmhouse is located just off of MO Hwy 72 on a 62 acre farm nestled against the Castor River. Here you and your companion(s) can experience the quiet and relaxing life on a farm with plenty of adventure awaiting just around the bend. Sit and enjoy a sip of coffee or tea on the front porch while watching the cattle graze the pasture across the road next to a rustic white barn or venture about 3 miles to the largest privately owned lake in Madison County. Oh yes, enjoy your stay!

Superhost
A charming log cabin is set amidst lush trees, featuring a green metal roof and a welcoming porch. Stone pathways guide to an outdoor seating area with a picnic table, complemented by a fire pit surrounded by natural stones, creating an inviting outdoor environment.
Cabin in Lesterville Township
4.87 out of 5 average rating, 347 reviews

Black River Cozy Cabin

This quaint cozy cabin offers a retreat from life's hustle and bustle with breathtaking views and a serene environment. The Black River Cozy Cabin is perfect for family vacations or a romantic get-away. With a secluded lake out the back door and two fire pits for roasting marshmallows and hot dogs, there are plenty of outdoor activities without even leaving the property. Of course, there is always more to explore in the area as well; including the Black River, which is just a short hike away.

Superhost
A 20-foot yurt is situated among bare trees, surrounded by nature. A spacious wrap-around deck enhances outdoor living. The structure features a circular design with a clear dome top and a single door visible. Nearby, a separate area can be seen, possibly for cooking or relaxation.
Yurt in Fredericktown
4.91 out of 5 average rating, 109 reviews

St Francis River: The Blue Yurt and Hot Tub

Let your adventure begin inside the tranquil experience of this 20 ft yurt. Don't let the space fool you, the uniquely curved walls give ample space for a romantic getaway or a relaxing time with friends. The clear dome top provides a magical viewing experience from the queen size bed. The yurt is nestled in the heart of the Ozark Mountains. The expansive, romantically lighted, wrap-around deck provides a panoramic view of the St. Francis River where you can immerse yourself in the hot tub.

Guest favourite
An outdoor fire pit area is surrounded by a grassy lawn, framed by lush greenery. Two red Adirondack chairs are positioned on a natural stone surface, offering a cozy spot to relax. The sky is bright with fluffy clouds, adding a serene ambiance to the scene.
Cabin in Fredericktown
4.98 out of 5 average rating, 102 reviews

Harmony Hills Cabin on The Little St Francis River

Rustic Cabin overlooking the Ozark Mountains. The Little St. Francis River is only a short walk from the scenic porch. Enjoy the serenity of nature or sit by the bonfire and enjoy a peaceful gaze at the stars. Cozy and well stocked, you'll find this place a home away from home. Bring your fishing poles, hiking boots, swim gear, kayak, a book or just kick back and relax. Please note, *** THERE IS NO WIFI or LIVE TV *** it isn't available in the area. We offer DVDs, books and games.

Top guest favourite
Several alpacas are gathered in a sunny pasture, showcasing their soft, fluffy coats. The group includes a variety of colors, from creamy white to rich brown, with their distinctive faces and calm expressions visible. A fenced area and grassy landscape are seen in the background.
Farm stay in Arcadia
4.93 out of 5 average rating, 142 reviews

Alpaca Farm Stay

Come see the baby alpacas and stay at the most tranquil and private getaway retreat in Arcadia Valley, Missouri and reconnect with nature. Our alpaca farm is nestled on over 28 acres in the Saint Francois Mountains next to the Mark Twain Natl Forest. The lodge is the perfect place for fishing on our 4-acre lake, relaxing after a long day of hiking, and meeting a small herd of alpaca. Your group will have an opportunity for a one-hour meet-and-greet scheduled at your convenience.

Top guest favourite
The treehouse structure is elevated, supported by stilts, with large windows that reflect the surrounding greenery. The exterior features a combination of wood finishes, and warm lighting casts a welcoming glow in the evening. The pathway leads through the natural landscape to the entrance.
Treehouse in Perryville
5 out of 5 average rating, 682 reviews

Romantic Treehouse Retreat w/ Hot Tub

The TreeLoft is a secluded luxury treehouse designed for rest, romance, and reconnection. Nestled in a private forest just 1 hour from St. Louis in Southeast Missouri, it blends upscale comfort with immersive nature. Located 20–35 minutes from hiking, wineries, and dining, this peaceful retreat invites you to unplug, slow down, and reconnect in intentional privacy. Making the TreeLoft perfect for romantic getaways, personal retreats, anniversaries, or creative escapes.

Top guest favourite
A warm living area is furnished with a brown leather couch and a patterned area rug. A vintage bicycle is displayed on the wall, enhancing the space. Natural light filters through the window, reflecting off the polished wooden floors.
Bungalow in Ironton
4.97 out of 5 average rating, 144 reviews

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

Classic Craftsman meets modern comfort at the Ironton Bungalow. This charming 2 bed, 1 bath home blends timeless character with thoughtful updates in a quiet Arcadia Valley neighborhood. Enjoy cozy interiors, a fully equipped kitchen, fast Wi-Fi, and a highlight front porch perfect for morning coffee or evening unwinding. Just minutes from Shepherd Mountain Bike Park, hiking, and downtown Ironton—an ideal home base for adventure or relaxation.

Superhost
Cabin in Leadwood
4.92 out of 5 average rating, 157 reviews

The Pallet Factory (Cabin 1)

Come and have some fun at our semi- private cabin that sits on a stocked pond. We are dog friendly only. This property has 2 additional cabins and 2 houses available if needed. Each space has 5 acres creating a semi private experience to relax and enjoy the outdoors. ***please note due to drought, pond levels are extremely low.****

Popular amenities for Fredericktown holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Madison County
  5. Fredericktown