Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

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

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Guest favourite
The log cabin, featuring a red metal roof, is nestled in a serene rural setting. Soft outdoor lighting highlights the front porch, where a seating area is visible. Lush grass surrounds the cabin, enhancing its secluded atmosphere. Trees provide a backdrop to the peaceful surroundings.
Cabin in Annapolis
4.93 out of 5 average rating, 42 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!

Top guest favourite
A rustic home built of natural wood is framed by blooming pink trees and lush green grass. The structure features a spacious porch with seating, while large windows allow views into the inviting interior.
Farm stay in Steelville
4.99 out of 5 average rating, 163 reviews

Yeary Farms Milt's Place with Private Beach!

An Ozark Oasis in the middle of a working cattle ranch, this custom designed home offers deluxe comfort. With multiple decks, porches and views out every window, this home is the perfect getaway for romantic retreats, family and friends to relax and make memories, artists and writers to host workshops or retreats, or even the single person to just get away from it all. Good dogs welcome, $35 per dog per week, fee collected separately at time of check in. Look for Yeary Farms site for more info.

Superhost
The entrance of the cabin showcases a stone patio with two seating areas. A black door is framed by wooden logs, while wicker and wooden chairs are positioned on either side, adorned with decorative cushions. Flower baskets hang by the windows, adding a welcoming touch.
Cabin in Lesterville Township
4.85 out of 5 average rating, 359 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
Yurt in Fredericktown
4.9 out of 5 average rating, 116 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.

Top 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, 153 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 several surrounding conservation sites. Bring your fishing pole and kayak! End your day relaxing by the fire pit and watching the sunset on the lake. We now offer event rentals for elopements, small wedding receptions, and small family reunions up to 18 people for an additional fee (message for details).

Guest favourite
Camper van/Motorhome in Annapolis
4.98 out of 5 average rating, 51 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
Home in Lesterville
4.84 out of 5 average rating, 148 reviews

Black River Dobbins House & Pavilion, Lesterville

This one of a kind historic home is located in the heart of Lesterville within walking distance to the local stores and restaurants. Included with stay is a private pavilion located on the crystal clear Black River less than a mile away. If floating of any kind is on your agenda, free shuttle to the house is available from some of the local campgrounds when you use them to navigate the black river. This home is just minutes away from Johnson's Shut Ins State Park and Elephant Rocks.

Top guest favourite
Treehouse in Perryville
5 out of 5 average rating, 696 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.

Top guest favourite
A modern treehouse is illuminated under the evening sky, showcasing a combination of metal and wood exterior elements. Stairs lead up to the entrance, while surrounding trees provide a natural backdrop. Soft lighting defines the structure's features, contributing to a relaxing ambiance.
Treehouse in Perryville
4.95 out of 5 average rating, 195 reviews

Rustic reTREEt Treehouse Getaway

This treehouse features a gorgeous floor-to-ceiling stone indoor/outdoor fireplace, vaulted ceiling, and many large windows which provide natural light and beautiful views. The interior design fuses natural elements of wood and stone, with a more refined and polished urban country look. A partition wall creates intimate spaces w/in this large (950 sq.ft.) open floor plan. Highlights: king size bed, corner claw tub, rainfall shower, reading area, 65" TV, large deck,BBQ grill and WIFI.

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, 103 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.

Guest favourite
Cabin in Fredericktown
4.89 out of 5 average rating, 325 reviews

Hot tub/ Blissful Beaver River Cabin

Remodeled remote cabin with an antique modern feel, large deck overlooking the St.Francios River. Soak your cares away in the Hot Tub. The river is great for kayaking and fishing. Enjoy a peaceful nature get away. Bring your fishing poles, a book, kayaks and disconnect from the hustle and bustle of everyday life! We’re close to Silver Mines, Millstream Gardens, Taum Sauk Mountain, Amidon Conservation, Elephant Rocks, only 10 miles to Ironton or Fredericktown for food and drinks!

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, 133 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.

Popular amenities for Annapolis holiday rentals

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