Vacation rentals in Annapolis

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Top-rated vacation 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 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 homes 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.

Top 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, 81 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
4.87 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.

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, 187 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.

Guest favourite
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, 103 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
Treehouse in Greenville
5 out of 5 average rating, 318 reviews

Private HOT TUB "The Roost" A Secluded Treehouse

"The Roost" is a modern treehouse 2 hrs south of St Louis near Wappapello Lake. Yes it has indoor plumbing & running water. Accommodates two adults, has a fully equipped kitchen, and breakfast items are provided for you to cook. Surrounded by thousands of acres of national forest. Observe wildlife sightings from the deck while soaking in the private hot tub, sleep comfortably in a queen size pillowtop Serta bed on a Motion Air base, and relax as you enjoy the ambience of the fireplace.

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, 102 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
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, 130 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, 141 reviews

Alpaca Farm Stay (save 10% for non-refundable)

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.

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
The cabin exterior features a metal roof and a combination of dark wall panels and natural wood accents. Two windows sit symmetrically on either side of the white front door, framed by wooden shutters. A gravel path leads up to the entrance, surrounded by a wooded area.
Place to stay in Annapolis
5 out of 5 average rating, 32 reviews

Cabin #1 Unique Cabin right by the Black River

Cabin #1: Tucked away in the mountains of Annapolis, less than a 1/4 mile away from K Bridge access. Come stay at our primitive cabin for one of your most memorable glamping experiences on the beautiful Black River. This cabin rental is almost an all-inclusive. The only things you need are food, drinks and towels. Everything else is included. There is no need to worry about firewood, charcoal, propane, cooking utensils, etc.

Popular amenities for Annapolis vacation rentals

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