Vacation rentals in Annapolis

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Top-rated vacation rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A lush green lawn is highlighted, dotted with trees and shrubs. In the distance, a treehouse structure and a pavilion are visible, surrounded by nature. A small garden area with diverse foliage is positioned in the foreground, contributing to the serene outdoor setting.
Treehouse in Bunker
4.96 out of 5 average rating, 163 reviews

Almost Heaven Treehouse

Featured in St Louis Magazine Spring 2022! Previously Parade Magazine and Only in Missouri! Nestled on the banks of Big Creek in the heart of the Missouri Ozarks and the Roger Pryor Pioneer Back Country, sits the Almost Heaven Treehouse. This quaint and rustic space is a must visit for those who love the great outdoors. Whether you want to relax in the creek, swim, hike, fish, paddle float,or ride atvs or s x s, this is the place for you!! This cabin is located 6 miles off pavement.

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, 88 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.

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
4.85 out of 5 average rating, 364 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.

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, 36 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
4.89 out of 5 average rating, 117 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
Train in Fredericktown
4.95 out of 5 average rating, 21 reviews

Unique Train Caboose Stay | Firepit & Loft

The attraction isn't just nearby—it's where you'll stay. Step aboard an authentic train caboose and enjoy a getaway unlike any ordinary cabin or hotel. Climb into the cupola, discover railroad history, play yard games, stargaze around the firepit, and make memories together. Families love the scavenger hunt and spacious yard, while couples enjoy the cozy atmosphere. Minutes from local dining, Elephant Rocks, hiking, and outdoor adventures. More than a stay—it's a destination experience.

Top 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/RV in Annapolis
4.98 out of 5 average rating, 52 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.

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, 701 reviews

Private Treehouse Retreat | Hot tub

The TreeLoft is the first of two treehouses at BaseCamp—designed for cozy seclusion, romance, and rest. Nestled in a private forest just 1 hour from St. Louis, it blends upscale comfort with immersive nature, while still being 20–35 minutes from hiking, wineries, and dining. ✨Our NEW treehouse, The TreeRise, offers an even more elevated, spacious experience at BaseCamp. Perfect for romantic getaways, anniversaries, personal retreats, and intentional escapes to unplug and reconnect.

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, 134 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.

Guest favourite
A covered porch offers expansive views of rolling hills and a glistening pond. A swing chair is positioned to the side, inviting relaxation, while flower beds with vibrant blooms border the entrance. Sunlight illuminates the landscape, enhancing the natural beauty of the surroundings.
Cabin in Fredericktown
4.96 out of 5 average rating, 337 reviews

Cabin on the farm

The Space Rustic charm meets the serene beauty of the Ozarks in this magical setting overlooking our farm, offering a perfect retreat for rest or a base camp for your next adventure. Inside, you'll find a cozy living space decorated with modern farmhouse charm, complete with a warm electric fireplace. Relax in the comfortable king-size bedroom after a day of exploring. The cottage also includes a well-appointed bathroom and a functional kitchenette for your convenience.

Guest favourite
Cabin in Ironton
4.97 out of 5 average rating, 34 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.

Popular amenities for Annapolis vacation rentals

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