Vacation rentals in Annapolis

4.97 out of 5 average rating, 102 reviews

An aerial view captures the carriage house with a spacious deck and an umbrella-covered table, complemented by decorative shrubs lining the property. The driveway accommodates multiple vehicles, while a flag adds a touch of charm to the inviting exterior.

Home in Farmington

Columbia Street Carriage House

Located in historic downtown Farmington, minutes away from restaurants, wineries, shops, and parks. Our newly renovated carriage house has much to offer! Our 2+ acre yard is fully fenced with a gated entrance offering privacy, a fire pit, covered patio, and large deck. The city park is located next door with a private acces gate offering basketball courts, pickle ball, tennis, swing sets, pavilions and playgrounds. Come enjoy a relaxing weekend or stay a week exploring the area attractions.

4.61 out of 5 average rating, 93 reviews

The exterior of a charming cabin is surrounded by lush greenery and wildflowers. A red metal roof contrasts with the stone facade, while a wooden bridge leads to the entrance. Tall trees provide shade, creating a serene setting in a spacious yard.

Cabin in Middle Brook

Stone Cabin and Snow Hollow Lake

Relax with the whole family at this peaceful cabin on Snow Hollow Lake. Built in 1916, this cabin has access to swimming, fishing, and kayaking just around the corner. Enjoy the spacious backyard, roast marshmallows around the campfire, and BBQ on the screened in back porch. Remodeled in 2022 with modern amenities, this cabin has everything you need for the perfect getaway. Explore: Elephant Rock State Park: 3 miles Johnson’s Shut-Ins State Park: 12 miles Shepard Mountain Bike Park: 7 miles

4.98 out of 5 average rating, 43 reviews

A serene bedroom showcases a spacious bed layered with soft linens and decorative pillows. Two bedside lamps provide warm illumination, complemented by artwork depicting mountains on the wall. Natural light filters through a set of large windows, framed by dark curtains, enhancing the calm atmosphere.

Bungalow in Ironton

Main Street Retreat, walk to downtown Ironton

Welcome to Mainstreet Retreat, this two bedroom bungalow is nestled a few blocks from the town square of Ironton. There are several shops and restaurants in close proximity, the home features a covered front porch to enjoy mountain views, the bathroom has recently been updated! This home has a patio in the back, with a stainless steel firepit, off street parking, the property is only a short drive away from several of the state parks around the area, Elephant Rocks being about 5 minutes away!

Cabin in Lesterville Township

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.

4.87 out of 5 average rating, 334 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.

4.97 out of 5 average rating, 179 reviews

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

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.

4.63 out of 5 average rating, 19 reviews

Floor-to-ceiling windows frame a serene view of the surrounding trees and sky. A warm, electric fireplace offers an inviting glow, while a cozy sleeping area features a quilted bedspread. A television hangs on the wall, and a small table and chairs are positioned nearby.

Treehouse in Annapolis

RIVER and SKY Treehouse -Hot tub-Amazing Views-

The River and Sky cabin offers a unique experience with floor to ceiling windows that brings the outdoors in overlooking the St. Francois River. The small cabin has everything you need for a weekend alone, a romantic getaway, or a relaxing time with friends. Sip your morning coffee overlooking the river. Create a rustic outdoor dining experience by cooking with the electric grill under the covered outdoor kitchen. Immerse yourself in the hot tub as eagles fly overhead, or stargaze at night.

4.98 out of 5 average rating, 49 reviews

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.

Camper/RV in Annapolis

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.

4.94 out of 5 average rating, 127 reviews

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

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.

5 out of 5 average rating, 21 reviews

The image displays the entrance to the E-5 Riverway B&B. A decorative green wreath is hung on the door, which is painted black. A sign indicating 'NO SMOKING' is positioned below the wreath, visually contrasting with the door's color.

Apartment in Ellington

Riverway Rentals E5

This unique place has a style all its own. Centrally located between Current River, Black River, and Clearwater Lake. This small, yet cozy apartment is the perfect getaway during the summer when you’re ready to enjoy the water or even during the colder months. One bedroom with a queen sized bed and a pull out futon in the living room. The on-site pool is a perfect addition for when you’re wanting to cool down after a hot day! NO SMOKING. NO PETS. Check out one of our other units!

4.88 out of 5 average rating, 17 reviews

Tiny home in Patterson

Rustic Tiny Home

Get away from it all when you stay under the stars. This sweet little accommodation is rustic on the inside and nestled in the Missouri Southeast close to the historic Sam A. Baker State Park. Two full hook up RV sites are on either side of the tiny home, allowing for camping of family or friends. Your host is close by in a home next door allowing us to quickly meet needs that may surface during your stay. The unit does have a washer/dryer as well. Note: RV rental is separate.

4.85 out of 5 average rating, 260 reviews

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

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.