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, 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

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, 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
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, 143 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, 131 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
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, 143 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
A spacious sleeping area is showcased with a textured blanket draping over the bed. In the background, cozy seating includes two armchairs positioned near a small table, with a decorative shelving unit filled with books. Large windows enhance natural light throughout the space.
Treehouse in Perryville
4.95 out of 5 average rating, 182 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.

Guest favourite
The exterior of a single-story house is displayed, featuring a light gray siding and a triangular roof. A welcoming front door with a decorative glass insert is visible, flanked by windows. Low shrubs and greenery line the entrance, enhancing the inviting appearance.
Home in Annapolis
4.93 out of 5 average rating, 28 reviews

Kelley’s Kottage full house, 3 bedroom, sleeps 7

Relax with the whole family at this peaceful place to stay. This family friendly, dog friendly house is 5 min from K-Bridge on Black River. There is a playground next door, and basketball court across the road. We have a fire pit, bbq grill, spacious back yard for playing catch, corn hole, or just relaxing and enjoying the country air. No tents or vehicles allowed in the yard. There is a video doorbell on the front door, and one pointed at the back yard.

Guest favourite
A newly built cabin with a dark exterior features three windows, two of which are adorned with blue chairs on the porch. A broad wooden deck surrounds the entrance, framed by natural landscaping that includes grass and small flowers.
Cabin in Patterson
4.92 out of 5 average rating, 12 reviews

Hideaway #4

Relax with the whole family at this peaceful newly built cabin. this cabin has a beautiful scenery where you can watch the beautiful sunsets. Sam A Baker State Park is located 4 miles away, Clearwater Lake is 14 miles, Saint Francis River within 5 miles and for your connivence Dollar General within 1 mile. We have catch and release fishing on property at designated area (children must be accompanied by an adult) and we have firewood and ice available

Top Guest favourite
A welcoming front porch features two light green chairs and a small table, framed by a white railing. Outdoor string lights are hung overhead, providing soft illumination. Windows with multiple panes offer views into the cozy interior space.
Bungalow in Ironton
4.97 out of 5 average rating, 145 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.

Popular amenities for Annapolis holiday rentals

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