Vacation rentals in Middle Brook

Hidden Hollow Cabin

Nature and adventure is awaiting you at this 2 bedroom cabin. Nestled in a tranquil setting, this beautiful retreat features 1 king bed and 2 full beds. We offer AC, electric and wood heating, as well as a jetted bathtub. The cabin is near popular sights such as Taum Sauk Mountain, Elephant Rocks, and Johnson Shut-Ins. This venue is perfect for nature lovers. We offer hiking trails, a 9 acre lake, hunting, kayaking, swimming, fishing, and relaxing at this beautiful property. NO FIREWORKS ALLOWED

Pickleball Cafe-Courtyard Suite

The Courtyard Suite is designed to provide a boutique hotel experience with three thoughtfully curated rooms, each offering a blend of comfort and style. One of the highlights is the pink refrigerator that adds a pop of color and personality to the space. Whether you're looking for a peaceful retreat or a home base to explore the town, The Courtyard Suite is the perfect choice. Enjoy the bustling atmosphere of the coffee shop below, and experience the charm of small-town living during your stay

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.

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!

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.

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.

The Olde Homestead

Take a break and unwind at this peaceful oasis. The Olde Homestead just newly remodeled offers many amenities and is perfectly located in the country just on the outskirts of city limits. A large deck in front, a patio in the back and a fire pit under the trees allow you to enjoy the great outdoors. The garage has a ping pong table, a bean bag toss game and a place to store your bicycles. Relax on the reclining sofa while watching the smart Roku TV or play one of the many games provided.

The Sutton House

Come enjoy this beautiful spacious Victorian built in 1915. The whole group, or just a couple, will enjoy easy access from this centrally located home. Sitting at the south base of Shepherd Mountain you will have easy access to hiking and Shepherd Mountain Bike Park. Elephant Rocks, Johnson Shut-ins and Taum Sauk state parks are minutes away. Only 2 blocks from Main St. you will be close to restaurants, shopping, coffee shops and special events happening at the courthouse square.

Luxury Cabin Sleeps 6 w/ Hot Tub and Outdoor Movie

Welcome to our Beautiful Luxury Cabin in the Woods—more than just a place to stay, it's an unforgettable experience. Nestled on 9 private acres, this custom-built, Scandinavian-inspired retreat offers the perfect blend of comfort and adventure. While the property features just one other guest cabin nearby, there are NO SHARED AMENITIES, ensuring you have complete privacy during your stay. The cabin is near Onondaga State Cave Park, Meramec River, Float Trips, Wineries and local dining.

The Tiegen Rae: cozy mountain cabin w/ huge views

Take it easy at this unique and tranquil getaway. "The Tiegen" is a beautiful A-frame cabin sitting on 20 acres at the top of Anderson Mountain. Imagine drinking your morning coffee sitting in a rocking chair and enjoying the breathtaking view of the Mark Twain National Forest. Or picture lighting an evening fire to enjoy the sounds of the woods with your favorite drink. This cabin will not disappoint and boasts full amenities to go along with your glamping adventure.

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

Classic Craftsman meets modern comfort at the Ironton Bungalow. This charming 2 bed, 1 bath home blends timeless character with thoughtful updates in a quiet Arcadia Valley neighborhood. Enjoy cozy interiors, a fully equipped kitchen, fast Wi-Fi, and a highlight front porch perfect for morning coffee or evening unwinding. Just minutes from Shepherd Mountain Bike Park, hiking, and downtown Ironton—an ideal home base for adventure or relaxation.

Modern Treehouse • Hot Tub • Private Escape

The TreeRise is a secluded luxury treehouse created for quiet moments and meaningful connection. Just 1 hour from St. Louis in Southeast Missouri and 20–35 minutes from hiking trails, wineries, and dining, this private forest retreat blends upscale comfort with nature. Thoughtfully equipped for rest, romance, and renewal, the TreeRise welcomes you to unplug, slow down, and reconnect—wrapped in trees, stillness, and intentional privacy.