Holiday rentals in Annapolis

4.95 out of 5 average rating, 144 reviews

Treehouse in Bunker

Almost Heaven Treehouse

Featured in St Louis Magazine Spring 2022! Previously Parade Magazine and Only in Missouri! Nestled on the banks of Big Creek in the heart of the Missouri Ozarks and the Roger Pryor Pioneer Back Country, sits the Almost Heaven Treehouse. This quaint and rustic space is a must visit for those who love the great outdoors. Whether you want to relax in the creek, swim, hike, fish, paddle float,or ride atvs or s x s, this is the place for you!! This cabin is located 6 miles off pavement.

5 out of 5 average rating, 266 reviews

Treehouse in Greenville

Five star secluded Treehouse-custom built-HOT TUB!

"The Roost" is rustic but not primitive 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 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.

4.96 out of 5 average rating, 53 reviews

Tiny home in Annapolis

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.

Cabin in Lesterville Township

4.88 out of 5 average rating, 314 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.

Serviced apartment in Van Buren

5 out of 5 average rating, 207 reviews

The Bonney House BnB

Current River retreat one bedroom open concept apartment w/ kitchenette. It has a gas fireplace & 55" TV. The kitchenette has microwave oven, coffee pot w/ filters & coffee, electric skillet, fridge w/ icemaker and basic dishes. The bathroom has a shower only. Apt has covered patio with outdoor dining & gas grill. You have access to wood firepit w/seating & picnic table. There's also a pavilion w/gas firepit & table w/seating overlooking Current River Bay. No smoking in apt. No pets.

5 out of 5 average rating, 123 reviews

Cabin in Ironton

The Valley Getaway Cabin:

Welcome to the most private getaway retreat in the beautiful Arcadia Valley, MO. Settled on 80 acres of wildlife and walking trails. The cabin is the perfect place to enjoy a long day of fishing and end the day with a relaxing bonfire with friends and family. To go along with the many activities to do while staying at the cabin, there are also many things to enjoy just a few miles away. From visiting elephant rocks for a peaceful walk to visiting the famous Shepard mountain bike trail.

4.93 out of 5 average rating, 123 reviews

Cabin in Redford

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.

4.81 out of 5 average rating, 36 reviews

Cabin in Annapolis

Panther Den Cabin is found 4 mile from K Bridge

The Panther Den is a brand new Cabin that is only 4 miles for Black River and Hwy K Campground. Cabin has two lofts for sleeping that kids will love!! Annapolis, Missouri is in the middle of tons of attractions and places to visit. Johnson's Shut-Ins State Park, Elephant State Park, Taum Sauk State Park and Sam A. Baker State Park are all within 30 minutes. Wappappello and Clearwater Lake are a short drive as well. Fire pit, BBQ grill, and picnic table comes with the Cabin.

4.93 out of 5 average rating, 134 reviews

Farm stay in Arcadia

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.

4.87 out of 5 average rating, 246 reviews

Home in Ironton

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.

5 out of 5 average rating, 635 reviews

Treehouse in Perryville

TreeLoft at BaseCamp - Nature + Luxury

Welcome to the TreeLoft experience! This is a custom built luxury treehouse for two. It is our hope that upon your stay you will be reconnected to nature and to the one you came with. We created the TreeLoft with an inspired state of mind, and we are hopeful that same inspiration will be experienced and reflected during your stay. Go to sleep counting stars and wake up with the trees! We can't wait to provide you with the TreeLoft experience! We rise by lifting others!

Place to stay in Annapolis

5 out of 5 average rating, 28 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.

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Popular amenities for Annapolis holiday rentals

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Other great holiday rentals in Annapolis

Tiny home in Arcadia

4.6 out of 5 average rating, 5 reviews

Peace Retreat

ElijahRating, 5 stars1 month ago

We had a wonderful time it was very beautiful ,private and more than accommodating,the area is close to Ironton and state parks and was a amazing great little place to stay!

Cabin in Annapolis

4.89 out of 5 average rating, 36 reviews

FS Rental #3 Annapolis, MO Black River

JenniferRating, 5 stars3 weeks ago

The cabin was perfect for what we needed. We ordered fire wood and Justin had it waiting when we arrived:) My only warning is of the train pull off, with younger kids they got very scared the first time, it gets loud and clanky. But after the intial scare, it was fine and had no problems sleeping through the night. Beds are very comfy.

4.84 out of 5 average rating, 89 reviews

Cabin in Lesterville

R & S Cabin on the beautiful black river.

ValerieRating, 5 stars8 months ago

Our family of 5 had a wonderful stay at this cabin! The surroundings were quiet and peaceful, the river was gorgeous, and the cabin was cozy and rather spacious! We had a campfire in the firepit and watched a few of the DVDs (big selection!). The kids had fun waving to the neighbors who drove by. Great weekend, great cabin, great host!

4.97 out of 5 average rating, 38 reviews

Home in Annapolis

Black River Cabin

KristieRating, 5 stars11 months ago

Had a lovely stay at Brian’s cabin. The cabin was very clean and was able to comfortably host 12 guests. The beds were very comfortable. I don’t think the pictures really do it justice. The cabin is very close to river access. We enjoyed swimming, bonfire, and watching the stars on the sand bar. The entire property is magnificent for star watching. The backyard has an excellent fire pit as well. Brian provided plenty of firewood. Saw a few deer, turkey, and bald eagle. My brother in law saw a bobcat. Went kayaking twice down the river, suggest black river outfitters at horseshoe ranch. My favorite part was the quiet and soaking up the surrounding forest. Take advantage of not having WiFi- it helped us all reset. I will absolutely return to this property. Made a ton of family memories. Thanks for hosting us!

4.99 out of 5 average rating, 71 reviews

Castle in Ironton

Historic Goulding Castle circa 1846

RobertRating, 5 stars3 months ago

We would highly recommend staying at this property. It is very cool and one of the best cleaned place we have stayed. Joan was very helpful and described her property spot on. We visited The Abbey for dinner which was great and learned about a tour of the property and we loved learning about the history or getting to see the chapel.

4.97 out of 5 average rating, 92 reviews

Cabin in Ellsinore

Cozy cabin with hot tub minutes from Current River

JosiRating, 5 stars1 week ago

absolutely wonderful stay! such a peaceful and private little place. they had the house stocked with anything you could think of and were very responsive and helpful! 100% recommend!

4.84 out of 5 average rating, 44 reviews

Cabin in Caledonia

Cabin D Village Country Store

KellyRating, 5 stars5 days ago

We had a great time here. So peaceful and quaint and they provided firewood. We were looking for somewhere to stay while we explored Taum Sauk, Elephant Rocks, and Johnsons Shut-ins. All of which were breath taking. If you are looking for a cabin hear Johnsons shut-ins look no further. Thank you Kelly!