Holiday houses 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
4.92 out of 5 average rating, 39 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 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, 140 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

Guest favourite
A charming red cabin is nestled among vibrant green trees, with a small, clear creek flowing gently nearby. The natural setting is complemented by lush foliage, creating a peaceful retreat in a rural environment.
Tiny home in Annapolis
4.94 out of 5 average rating, 65 reviews

Cabin on the creek - Glamping & Black River floats

This is a great place to unwind and unplug. Enjoy the sights and sounds of the creek flowing right in front of the cabin. This is a small cabin with 4 beds (2 bunkbeds) and full bathroom. The front porch overlooks the creek. The outdoor area includes a gazebbo, propane grill, table and firepit. Enjoy exploring the creek. The area is close to multiple outdoor gems including the Black River, Taum Sauk Mountain, Sam Baker State Park. There is no kitchen, but there is a mini-fridge and microwave.

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, 350 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, 35 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.

Top Guest favourite
A circular yurt is situated on a green lawn, featuring a wooden wraparound deck and a shaded area with a blue canopy. A stone fire pit is visible next to a picnic table and two adirondack chairs. Lush trees are seen in the background.
Yurt in Salem
4.97 out of 5 average rating, 197 reviews

Entire private Glamping Yurt next to forest

Pet friendly glamping in 1 of 2 private yurts next to the Mark Twain National Forest, is the perfect place to escape! Relax to all the sounds of nature the Mark Twain National Forest has to offer. Take in the stunning 360° views & peaceful surroundings from the 30'X30' wraparound deck! Spend your days hiking, kayaking, & all the things the area has to offer & your evenings around the campfire, watching the sunset & star gazing. If you love camping & modern amenities, you will love this place.

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, 110 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.

Superhost
A historic home features a welcoming front porch with white railings and decorative planters. Green grass surrounds the property, and mature trees provide shade. The pathway leads up to the entrance, framed by a peaceful natural setting.
Home in Lesterville
4.85 out of 5 average rating, 144 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.

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, 132 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
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
4.92 out of 5 average rating, 147 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
Tiny home in Patterson
4.92 out of 5 average rating, 24 reviews

Rustic Tiny Home

Get away from it all when you stay under the stars. This sweet little accommodation is rustic on the inside and nestled in the Missouri Southeast close to the historic Sam A. Baker State Park. Two full hook up RV sites are on either side of the tiny home, allowing for camping of family or friends. Your host is close by in a home next door allowing us to quickly meet needs that may surface during your stay. The unit does have a washer/dryer as well. Note: RV rental is separate.

Top Guest favourite
Cabin in Ironton
5 out of 5 average rating, 20 reviews

Hidden Hollow Cabin

Nature and adventure is awaiting you at this 2 bedroom cabin. Nestled in a tranquil setting, this beautiful retreat features 1 king bed and 2 full beds. We offer AC, electric and wood heating, as well as a jetted bathtub. The cabin is near popular sights such as Taum Sauk Mountain, Elephant Rocks, and Johnson Shut-Ins. This venue is perfect for nature lovers. We offer hiking trails, a 9 acre lake, hunting, kayaking, swimming, fishing, and relaxing at this beautiful property.

Popular amenities for Annapolis holiday rentals

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