Vacation rentals in Pilot Knob

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Top-rated vacation rentals in Pilot Knob

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Ironton
5 out of 5 average rating, 25 reviews

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

Top guest favorite
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
4.98 out of 5 average rating, 60 reviews

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!

Guest favorite
A beautifully restored stone castle sits amidst a backdrop of autumn foliage. The structure features tall windows and a distinctive tower, with greenery surrounding the gently sloping lawn that leads to a set of stone steps.
Castle in Ironton
4.99 out of 5 average rating, 88 reviews

Historic Goulding Castle circa 1846

***Please do not send any messages asking about weddings or events*** Amazingly restored Castle built by TR Goulding in the 1800’s. This unique and majestic property sits on 9 acres of Shepherd Mountain and connects to over 600 acres of hiking and biking trails on Shepherd Mountain. Enjoy beautiful views and a forest setting while still being minutes from restaurants and town. The property boasts priceless statuary, a rebuilt grotto, beautiful interior and the most peaceful grounds to enjoy.

Top guest favorite
A bright living area features a light-colored sofa paired with a dark armchair. Natural wood accents are present in the coffee table and flooring. Large windows bring in ample light, showcasing a nature-inspired wall mural and a small decorative plant.
Apartment in Ironton
4.97 out of 5 average rating, 69 reviews

Mountain View at Pickle & Perk

Who says camping has to be all bug spray & soggy sleeping bags?Located above popular Pickle & Perk, Mountain View is unique stay in the heart of Arcadia Valley, offering the feel of luxury in the middle of camping country. This is perfect for those who want to skip the hassle of setting up a tent but still be surrounded by the great outdoors. Sip on gourmet coffee, listen to the birds, and the gentle bustle of the cafe environment. You can have your s'mores and eat them in the lap of luxury.

Superhost
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
4.71 out of 5 average rating, 77 reviews

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.

Top guest favorite
Cabin in Leasburg
5 out of 5 average rating, 38 reviews

Luxury Couples Retreat with Hot Tub and Sauna

Welcome to Our Beautiful Couples’ Retreat “The Sunset Cabin” Nestled on 9 acres of private property. While the property features just one other guest cabin nearby, there are no shared amenities, ensuring you have complete privacy during your stay. Our modern yet cozy cabin was designed with one purpose relaxation and togetherness. Whether you’re celebrating a special occasion or simply escaping the noise of everyday life, this private retreat invites you to slow down and truly reconnect.

Guest favorite
A cozy living area is furnished with two brown leather sofas, adorned with decorative pillows. A painting depicting a pastoral scene hangs on the wall, complemented by a wooden accent wall. Twin table lamps provide soft lighting, enhancing the inviting atmosphere.
Home in Ironton
4.95 out of 5 average rating, 41 reviews

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.

Top guest favorite
The treehouse structure is elevated, supported by stilts, with large windows that reflect the surrounding greenery. The exterior features a combination of wood finishes, and warm lighting casts a welcoming glow in the evening. The pathway leads through the natural landscape to the entrance.
Treehouse in Perryville
5 out of 5 average rating, 700 reviews

Private Treehouse Retreat | Hot tub

The TreeLoft is the first of two treehouses at BaseCamp—designed for cozy seclusion, romance, and rest. Nestled in a private forest just 1 hour from St. Louis, it blends upscale comfort with immersive nature, while still being 20–35 minutes from hiking, wineries, and dining. ✨Our NEW treehouse, The TreeRise, offers an even more elevated, spacious experience at BaseCamp. Perfect for romantic getaways, anniversaries, personal retreats, and intentional escapes to unplug and reconnect.

Guest favorite
An aerial view captures the cabin surrounded by lush greenery and trees, with the St. Francis River visible nearby. The large deck and hot tub are seen, inviting relaxation, while the rustic red roof of the cabin complements the natural setting.
Cabin in Fredericktown
4.89 out of 5 average rating, 327 reviews

Hot tub/ Blissful Beaver River Cabin

Remodeled remote cabin with an antique modern feel, large deck overlooking the St.Francios River. Soak your cares away in the Hot Tub. The river is great for kayaking and fishing. Enjoy a peaceful nature get away. Bring your fishing poles, a book, kayaks and disconnect from the hustle and bustle of everyday life! We’re close to Silver Mines, Millstream Gardens, Taum Sauk Mountain, Amidon Conservation, Elephant Rocks, only 10 miles to Ironton or Fredericktown for food and drinks!

Top guest favorite
A serene lakeside view is presented, framed by tall trees casting shadows on the green grass. A flower planter adds a touch of color near the water's edge, with calm waters reflecting the surrounding nature and hills in the distance.
Cottage in Bonne Terre
5 out of 5 average rating, 118 reviews

2-bedroom cottage with a gorgeous lake view.

Come make memories at The Lake House. Whether it’s a getaway with the family, romantic weekend, or time with friends. You’ll be sure to enjoy this 2-bedroom, 1-bathroom cottage that accommodates up to 6 guests, a fully equipped Kitchen for all your cooking needs, coffee bar, and a Washer and dryer on site for guest use. Relax on the patio around the fire or enjoy the view of the lake while grilling. Located right next to Lakeview Park and not far from the Bonne Terre Mines.

Guest favorite
Cabin in Ironton
4.97 out of 5 average rating, 33 reviews

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.

Top guest favorite
The exterior of a two-story lodge is depicted, featuring a covered balcony supported by wooden beams. Rocking chairs are placed on the balcony, while windows are visible on each floor. A concrete path leads to the entrance, surrounded by open outdoor space.
Barn in Ironton
4.96 out of 5 average rating, 50 reviews

4 units available, book 1 unit or whole lodge!

Outside burning pits with benches while you enjoy the magnificent views we have to offer. Free WiFi, free parking, keyless entry on all doors, Dollar General store next door. Close by Elephant Rock state park, Johnson’s Shut-Ins state park, Shepard Mountain bike park. May book one unit or book the entire lodge whatever your vacation needs are! Coming soon Outside showers, bar and grill. We are here to accommodate you ! Beautiful Mountain View’s.

Popular amenities for Pilot Knob vacation rentals

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