Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

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Guest favourite
The exterior of Posey's Place features a charming log cabin with a red metal roof. A welcoming sign announces the property, surrounded by lush greenery and flowering plants. The cabin is set back from the road, offering a tranquil rural aesthetic.
Cabin in Annapolis
4.93 out of 5 average rating, 43 reviews

Posey's Place - Secluded Log Cabin

**Updated wood flooring has been put in and all carpet removed! Secluded Log Cabin on working farm. Located in rural Iron County just minutes from Black River, St. Francois River, Clearwater Lake, Elephant Rocks, Johnson Shut-Ins, & Shepherd Mt. Bike Park. Located just 11 miles from either K Bridge or Sam A. Baker Park, crystal clear water is waiting for you just minutes away. Take a relaxing float and return to the cabin for smores around the fire pit. Come and sit a spell at Posey's Place!

Guest favourite
A beautifully restored stone castle sits amidst a backdrop of autumn foliage. The structure features tall windows and a distinctive tower, with greenery surrounding the gently sloping lawn that leads to a set of stone steps.
Castle in Ironton
4.99 out of 5 average rating, 90 reviews

Historic Goulding Castle circa 1846

***Please do not send any messages asking about weddings or events*** Amazingly restored Castle built by TR Goulding in the 1800’s. This unique and majestic property sits on 9 acres of Shepherd Mountain and connects to over 600 acres of hiking and biking trails on Shepherd Mountain. Enjoy beautiful views and a forest setting while still being minutes from restaurants and town. The property boasts priceless statuary, a rebuilt grotto, beautiful interior and the most peaceful grounds to enjoy.

Top guest favourite
The exterior of a two-story cabin is displayed, featuring a wraparound deck supported by wooden posts. A gravel area is visible underneath, with a set of red chairs positioned on the deck. The cabin is surrounded by trees, providing a natural setting.
Cabin in Silva
5 out of 5 average rating, 37 reviews

The Cozy Cabin

Peaceful , family-friendly cozy cabin. Take a short drive to enjoy river fun, canoe and kayaking. Step outside in the morning onto the wraparound deck with a cup of coffee and listen and enjoy nature. Take a hike on the paths, roast marshmallows, make s’mores and hotdogs by the large fire pit, and many more things out in nature. If you’re looking for a peaceful getaway from the city or a night to rest on your way to wherever. Our cabin is also very unique with 3 full hookup campsites.

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
4.86 out of 5 average rating, 122 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
The exterior of a rustic grain bin house is showcased, featuring a stone and wood entryway with a covered porch. A grill is positioned nearby on a gravel patio, while trees are visible in the background, providing a natural setting.
Dome in Piedmont
4.75 out of 5 average rating, 40 reviews

The Grain Bin in Piedmont-Clearwater Lake-King Bed

Feel refreshed when you stay in this rustic gem a very unique grain bin! Great location-Just a few minutes from Clearwater Lake, Black River, St. Francis River, Sam A Baker, Lon Sanders Canyon. Walking distance to flea market. Only 1/2 mile to Pine-Hill drive in, 1 mile to Dollar General & close to several good restaurants. 3 sleeping areas , 2 baths and is fully stocked. Has great high speed wi-fi. Cook dinners in the kitchen, BBQ on the grill, watch tv or hang out on the porch or deck!

Guest favourite
A bright blue camper is set amidst lush greenery, accompanied by a patio featuring four adirondack chairs in vibrant colors. A covered outdoor kitchen area is visible nearby, alongside a propane grill, emphasizing a functional outdoor space for gatherings.
Camper van/Motorhome in Annapolis
4.98 out of 5 average rating, 53 reviews

The Happy Camper - Glamping & Black River floating

A great place to unplug and get away from it all! The Happy Camper includes a covered outdoor kitchen area, a firepit and additional beds in the adjacent cabin. The location is located nearby numerous outdoor gems including the Black River, Taum Sauk, Mountain , Sam Baker State Park, the Ozark Trail and mountain biking areas. The property has a year-round creek flowing through it to enjoy and explore. The adjacent "Cabin on the Creek" is also available to rent if you need more space.

Guest favourite
The scenic view captures the winding Black River surrounded by lush greenery, with sandy banks visible along the water's edge. The landscape is characterized by rolling hills under a partly cloudy sky, highlighting the natural beauty of the Ozark Mountains.
Cabin in Redford
4.94 out of 5 average rating, 136 reviews

The Cabin ❤️ at Black River View

Come experience total seclusion listening to the rapids of the Black River below 37 acres in the heart of the Ozark Mountains. If you like bonfires at night and having the place to yourself including plenty of side by side trails and a gun range to enjoy, you’ve found your place to get away. Overlooking the Black River and in site of the highest elevation point in Missouri this newly built in 2016 state of the art cabin has everything you need to entertain your family and friends.

Top guest favourite
A moonlit pool is surrounded by a well-maintained area, showcasing a spacious gazebo adorned with string lights. The inviting blue water reflects the warm glow, while lounge seating is provided within the gazebo, creating a cozy outdoor retreat.
Flat in Ellington
5 out of 5 average rating, 36 reviews

Riverway Rentals E5

This unique place has a style all its own. Centrally located between Current River, Black River, and Clearwater Lake. This small, yet cozy apartment is the perfect getaway during the summer when you’re ready to enjoy the water or even during the colder months. One bedroom with a queen sized bed and a pull out futon in the living room. The on-site pool is a perfect addition for when you’re wanting to cool down after a hot day! NO SMOKING. NO PETS. Check out one of our other units!

Guest favourite
Treehouse in Bismarck
4.94 out of 5 average rating, 52 reviews

248 Avalon Ranch Rd Treehouse C

You’ll treasure your time at this beautiful, peaceful place. A cabin on a lake with beach access and acres of property to explore. Enjoy the use of the canoe and kayaks. The lake is stocked with catfish, bass, bluegill and crappie for catch and release fishing. Spend time relaxing in the hot tub or around the fire pit during your stay with us. There are many state parks nearby to visit, and we are central to historic destinations in the area such as Caledonia and Ste. Genevieve.

Guest favourite
The cabin features a raised deck with wooden railings, providing ample outdoor seating space. An American flag is displayed on the front, and the surrounding grass is well-maintained. Sunlight filters through the trees, creating a pleasant outdoor atmosphere.
Cabin in Annapolis
4.85 out of 5 average rating, 47 reviews

Panther Den Cabin is found 4 mile from K Bridge

The Panther Den is a brand new Cabin that is only 4 miles for Black River and Hwy K Campground. Cabin has two lofts for sleeping that kids will love!! Annapolis, Missouri is in the middle of tons of attractions and places to visit. Johnson's Shut-Ins State Park, Elephant State Park, Taum Sauk State Park and Sam A. Baker State Park are all within 30 minutes. Wappappello and Clearwater Lake are a short drive as well. Fire pit, BBQ grill, and picnic table comes with the Cabin.

Guest favourite
Cabin in Ironton
4.97 out of 5 average rating, 36 reviews

The Tiegen Rae: cozy mountain cabin w/ huge views

Take it easy at this unique and tranquil getaway. "The Tiegen" is a beautiful A-frame cabin sitting on 20 acres at the top of Anderson Mountain. Imagine drinking your morning coffee sitting in a rocking chair and enjoying the breathtaking view of the Mark Twain National Forest. Or picture lighting an evening fire to enjoy the sounds of the woods with your favorite drink. This cabin will not disappoint and boasts full amenities to go along with your glamping adventure.

Top guest favourite
The exterior of the house features a well-maintained front porch with a stylish door and wooden steps leading to a spacious entrance. Surrounding the house, lush green grass provides a peaceful setting, with trees in the background adding to the serene ambiance.
Home in Annapolis
5 out of 5 average rating, 19 reviews

Ford Country - 3 bedroom 2.5 bath

Relax with the whole family at this peaceful place to stay. This house is in the country, tucked away on a quiet road. If you are looking to get away, unplug, and enjoy nature, this is the place for you. It is 5 minutes from Annapolis, and 10 minutes from K-Bridge. 3 bedrooms, sleeper sofa, 2.5 baths, full kitchen, washer and dryer. We are dog friendly with a Whole house generator for backup electricity.

Popular amenities for Annapolis holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Iron County
  5. Annapolis