Vacation rentals in Annapolis

4.95 out of 5 average rating, 144 reviews

A rustic treehouse is elevated on wooden stilts, surrounded by lush green trees. A spacious deck features several outdoor chairs for relaxation. Steps lead up to the entrance, while a cozy hammock is nestled beneath. The landscape includes a grassy area encouraging outdoor activities.

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.

4.96 out of 5 average rating, 53 reviews

A rustic cabin with a red exterior features a wooden deck adorned with several white rocking chairs. The cabin is surrounded by lush greenery, while a gentle creek flows nearby, reflecting the surrounding trees.

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

The serene Black River is depicted, featuring calm turquoise waters next to a sandy bank. A fallen tree branch extends into the water, while pebbles and rocks create a natural shoreline, illustrating a peaceful outdoor environment.

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.

5 out of 5 average rating, 18 reviews

A fire pit is filled with logs, partially charred and emitting light smoke. The surrounding area features scattered ashes and remnants from previous fires, set within a grassy landscape.

Cabin in Silva

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.

5 out of 5 average rating, 207 reviews

Apartment in Van Buren

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, 34 reviews

A water filtration system is mounted under the kitchen counter, featuring three distinct canisters labeled PP, GC, and CT. Each canister is connected by white tubing to ensure a clean water supply. The system is designed to provide purified water for cooking and beverages.

Home in Ellington

Welcome to The Pender Place!

Welcome to The Pender Place! The little house with a lot of perks! Enjoy a complete new kitchen, fully furnished with everything you need away from home including a three stage water filter system, coffee & tea bar, comfortable bedrooms, one with TV. Large Roku TV in living room, washer & dryer, front porch with lighting and seating, covered carport with additional off-road parking. Just a few blocks from local shops and businesses. We're located in the hub of the beautiful Ozarks!

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.

The cabin features a raised deck with wooden railings, providing ample outdoor seating space. An American flag is displayed on the front, and the surrounding grass is well-maintained. Sunlight filters through the trees, creating a pleasant outdoor atmosphere.

4.81 out of 5 average rating, 36 reviews

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

Three friendly alpacas are positioned in a grassy area, with a shimmering lake visible in the background. Their coats range from light brown to white, offering a gentle contrast against the natural landscape. The scene is framed by trees, hinting at the serene environment.

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

A spacious kitchen features dark blue cabinetry, complemented by a long wooden countertop. Large windows provide expansive views of the surrounding nature, while a stone fireplace is positioned in the corner, creating a functional and inviting space for cooking and gathering.

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.

4.98 out of 5 average rating, 113 reviews

Cottage in Lesterville

Cottage in the Ville

The "Cottage in the Ville," a charming, home away from home cottage, comfortably sleeps six and has two bedrooms. Just two hours south of St. Louis, MO, our beautifully decorated cottage, near the crystal clear Black River, is the perfect destination to get away from the hustle and bustle of city life. The “Cottage in the Ville” sits on two beautifully manicured flat acres of land with plenty of room to roam.

A clear river flows gently past a sandy bank, framed by lush green trees on either side. The bright blue sky is dotted with fluffy white clouds, creating a serene backdrop that invites relaxation and connection with nature.

4.89 out of 5 average rating, 18 reviews

Relaxing 3B Log Home- 15 min walk to Black River!

Welcome to Black River Escape Nestled in the woods just 2 hours south of St. Louis, this spacious log home offers rustic charm with modern comforts. Enjoy an open floor plan, cozy lodge-style furnishings, and ample deck space. Just up the hill from the Black River, it's perfect for relaxing, sharing meals, or playing games. Don't miss "Fireside," our outdoor pavilion featuring a grand stone fireplace.

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Popular amenities for Annapolis vacation rentals

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Other great vacation rentals in Annapolis

A serene natural setting is captured with a gently flowing creek bordered by smooth stones. Lush greenery and tall trees provide dappled shade, while vibrant red flowers add a pop of color along the water's edge. The clear water reflects the surrounding foliage.

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!

A modern kitchen space features dark cabinetry and a grey granite countertop. Stainless steel appliances include an oven and microwave. A wall-mounted television is positioned above the countertop, which is equipped with cooking utensils and a sink. Natural light streams in through a window.

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.

A tranquil outdoor area along the bank of a stream is depicted. Two rustic chairs sit on a grassy patch surrounded by lush greenery. The stream, flanked by smooth stones, reflects the dappled sunlight filtering through the trees overhead.

Campsite in Middle Brook

4.81 out of 5 average rating, 21 reviews

The Spot

JamieRating, 5 stars2 weeks ago

was a really nice place to stay for my family for the weekend. we really appreciated the hospitality

4.86 out of 5 average rating, 50 reviews

A fire pit surrounded by four teal chairs is nestled on a gravel surface. A wooden fence stands in the background, creating a private outdoor space ideal for gathering. The area is shaded by lush trees, adding to the serene environment.

Bungalow in Lesterville

FLOATING! Black River Bungalow (Lesterville, MO)

DanielleRating, 5 stars9 months ago

Thinking of going floating and need a place to stay?! STAY HERE!!! This was our 2nd year and we will stay a 3rd time next year. It's perfect for our large (14) group! Easy check in. Beds are comfy. We like how toilets are separate from showers. Good places to eat right next door. Also, Franklin Floats picks us up and drops us off at the doorstep.

4.97 out of 5 average rating, 38 reviews

A wooden sign features the text 'Black River Cabin' adorned with a silhouette of a deer. The shield-shaped design utilizes warm earth tones, blending elements of nature with a rustic cabin aesthetic.

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!

4.96 out of 5 average rating, 55 reviews

An expansive outdoor area is visible, featuring a gravel path leading towards a rustic building adorned with old advertising signs and memorabilia. The surrounding trees provide a natural backdrop, while the sky is partially cloudy with a moon visible on the left.

Home in Ellington

Antiques by the Lake

SarahRating, 5 stars5 days ago

Great place to stay and the value was amazing. We loved all the decorations and of course the pool!!

5 out of 5 average rating, 5 reviews

A serene forested area is depicted, characterized by tall trees with budding leaves. A neatly stacked pile of firewood is positioned against a natural stone wall, while a rocky patch of ground complements the earthy tones of the landscape.

Cabin in Des Arc

Inviting Des Arc Cabin w/ Fire Pit + Deck!

LeslieRating, 5 stars10 months ago

I booked this for a personal retreat so I could work on some life planning, get some writing in, and be out in nature to reconnect with my body. This place is a great location for accessing nature, and Michelle and Scott were wonderful! Because this is hosted by Evolve I expected it to be a little sterile, but the folks who live on the property and rehabbed the cabin were totally lovely and helpful and obviously put a lot of care into the place. It felt private and safe and it was nice to have the owners nearby. Lots of nature sounds, including owls. It rocked! I put a 4 star for check in because Google Maps did not take me to the right spot on the Highway since it is a newer address listing, but looking up the addresses listed on the mailboxes led me to the right place and it was a breeze from there. Would love to stay again!

The log cabin is set in a spacious yard, framed by trees and bordered by open fields. A gravel driveway leads to the entrance, while warm lighting emanates from the windows, creating a welcoming appearance against the natural surroundings.