Holiday rentals 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, 38 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
Cabin in Greenville
4.99 out of 5 average rating, 169 reviews

Cabin "The Fox Den" surrounded by forest w/HOT TUB

"The Fox Den" was designed just for couples...curling up by the fireplace or soaking in a hot tub in a screened-in porch, this unique 70's themed cabin in the woods, away from the stressors and noise of everyday life. Whether you're celebrating or just looking for an excuse to come for seclusion and quiet, the fox den is the ideal place to book for your romantic getaway, located 2 hrs. south of St Louis near Wappapello Lake. Breakfast items provided for guests to cook, including farm fresh eggs

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, 344 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, 186 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.

Top guest favourite
The exterior of a bungalow showcases a welcoming front porch adorned with string lights. A vintage bicycle is parked on the pathway, with greenery framing the entrance. The house features a distinct two-tone siding and a stone chimney, enhancing the quaint appeal.
Bungalow in Ironton
4.96 out of 5 average rating, 139 reviews

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

The Ironton Bungalow is on quiet neighborhood street in the heart of downtown. A block off Main St. you can walk to town square restaurants and coffee shops thru our backyard gate. Enjoy the front porch for relaxing with coffee. Centrally-located home in in the Arcadia Valley , just minutes from Johnson Shut-Ins, Elephant Rocks and Taum Sauk State Parks, Black River Floating, Shepherd Mountain Bike Park, Pilot Knob battlefield and Millstream Gardens. Take a look at our insta #irontonbungalow

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, 102 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 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.
Campervan/Motorhome in Annapolis
4.98 out of 5 average rating, 50 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
A modern cabin exterior is framed by a vibrant landscape. Light-colored siding is contrasted with a dark roof, and the entrance features a welcoming porch supported by wooden beams. Potted flowers add a touch of color, while windows allow natural light to fill the interior.
Cabin in Piedmont
5 out of 5 average rating, 64 reviews

By Clearwater Lake/Black River-Golf Range On-Site

One bedroom cabin loaded with amenities! Private location in a 12 acre field with wildlife to watch and also conveniently located a few blocks from Main Street. NO EXTRA FEES ADDED/no household chores! Free parking, plenty for boats and atv’s also No amenities left out-laundry facilities, all cooking supplies, stocked coffee bar, high speed internet, Netflix, plush king bed, rainfall shower head and more. Please note: a silicone heat pad is provided for all irons in the bathroom.

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, 129 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.

Superhost
A fire pit area is situated on a sandy patch, featuring logs arranged as seating and rocks surrounding the pit. The backdrop showcases a sunset over the distant hills, with trees and open fields framing the serene scene.
Home in Ironton
4.85 out of 5 average rating, 268 reviews

Mountain Cabin, Wow Views, King Bed, Hiking+

This serene countryside location is all yours to enjoy the beauty of the Missouri Ozarks with stunning views of the mountains. This fully equipped home offers plenty of room, great decks for grilling and relaxing, bon fire pit, and 8 private acres to explore and hike, located right next to Taum Sauk, and just a few miles to trails, Elephant Rock St. Prk, Johnson Shut-Ins, and local rivers and streams to swim and hike as well as ATV trails! Relax, unwind, and take in the view.

Top guest favourite
The exterior of a cozy cabin is showcased, surrounded by tall trees. A welcoming wooden door is framed by large windows. Two chairs are positioned on the front porch, inviting relaxation amidst the natural setting.
Cabin in Ellsinore
4.97 out of 5 average rating, 117 reviews

Cozy cabin with hot tub minutes from Current River

Cane Creek Cabin is located in Ellsinore, Missouri; minutes from the beautiful Big Springs National Park, Current River and Black River. If you’re looking for a secluded quiet getaway, look no further!! This cozy 432 sq. ft, studio cabin is the perfect getaway from the hustle and bustle of our fast paced world. Situated on 37 acres with a creek view, it’s the perfect location to unwind after a fun filled day at the river or just to getaway and enjoy the beautiful Ozarks.

Popular amenities for Annapolis holiday rentals

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