Holiday houses in Cherryville

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Top-rated holiday rentals in Cherryville

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

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Top Guest favourite

A rustic home built of natural wood is framed by blooming pink trees and lush green grass. The structure features a spacious porch with seating, while large windows allow views into the inviting interior.

Farm stay in Steelville

4.98 out of 5 average rating, 171 reviews

Yeary Farms Milt's Place with Private Beach!

An Ozark Oasis in the middle of a working cattle ranch, this custom designed home offers deluxe comfort. With multiple decks, porches and views out every window, this home is the perfect getaway for romantic retreats, family and friends to relax and make memories, artists and writers to host workshops or retreats, or even the single person to just get away from it all. Good dogs welcome, $35 per dog per week, fee collected separately at time of check in. Look for Yeary Farms site for more info.

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Top Guest favourite

A unique outdoor structure with an arched wooden door is surrounded by lush greenery. The landscape features manicured grass and stone walls, with decorative plants hanging near the entrance. Lawn games are set up nearby, providing recreational options in a tranquil natural setting.

Tiny home in Steelville

4.95 out of 5 average rating, 111 reviews

The Hobbit Hideaway

Have you ever wanted to live the simple laid back life of a Hobbit? Well,here is your chance. You will walk through the round wooden doors into the partial underground home,feeling more like a Hobbit with each passing moment. This beautiful tiny home is very private,sitting in the woods,while still having convenient access off Rte.8. Wether it's relaxing watching the deer,rabbits and squirrels play or rafting one of the nearby rivers with a local outfitter you will find this a great getaway.

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Guest favourite

A bright red tiny house is reflected in the calm water, surrounded by lush greenery. The property includes a private dock, equipped with a water slide and lounge chairs, enhancing the serene lakeside setting.

Tiny home in Rolla

4.95 out of 5 average rating, 575 reviews

Tiny Paradise on the Quarry

Come and enjoy the Tiny Paradise on the Quarry, as seen on HGTV's "Tiny Paradise" in 2017. House Beautiful Magazine's listed it as one of the TOP 50 Tiny Houses in the USA. Featured in People Magazine's HGTV special edition magazine. Missouri Life Magazine listed it as one of the top 9 gems in Missouri. Also featured as one of the four fall get-a-ways in 417 Magazine's. St. Louis Magazine listed it as the coolest Airbnb in their Aug/Sept 2019 issue. You are welcome to have more than two guest

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Guest favourite

A charming cabin exterior is framed by trees showing autumn leaves. A welcoming porch features wooden steps, outdoor seating, and decorative lighting. The cabin's natural wood siding and metal roof blend harmoniously with the surrounding landscape.

Cabin in St. James

4.84 out of 5 average rating, 179 reviews

Hawks Ridge Cabin

Hawk Ridge is a stunning custom 1.5 story with 3 bedrooms and 2.5 baths, handicap accessible situated on 14 private acres. It is minutes from St. James, Meramec Springs State Park with trophy trout fishing, wineries, hiking and golfing. Canoeing, kayaking, rafting, zip-lining and horseback riding are only 10 short miles away. This location has something for every. 41 miles from Ft. Leonard Wood 17 miles from Fugitive Beach 17 miles from Steelville (floating) 3 miles from Maramec Springs Park

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Top Guest favourite

The charming exterior of the house is framed by lush greenery and features a covered porch with colorful chairs. Well-maintained landscaping includes stone accents and flower pots, enhancing the inviting entrance. A concrete pathway leads to the front door, providing a welcoming approach.

Home in Steelville

4.97 out of 5 average rating, 59 reviews

Cozy Steelville Getaway!

Unwind at this cozy Steelville getaway after a day on the river. This charming house nestled on three acres is minutes from multiple river resorts (including Bass and Huzzah), shops, restaurants, hiking and parks. The house sleeps up to 7 people (1 queen, 1 full, 3 twin), and has a TV, wifi, full kitchen, washer & dryer, firepit area, multiple patios, and basketball hoop. It is a great choice for a family or a group of friends. The property has 3 outdoor cameras for additional security.

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Top Guest favourite

A modern cabin exterior is shown, featuring warm outdoor lighting and a combination of wood and metal materials. A spacious deck is accessible via steps, while a covered area with a grill and outdoor movie projector is visible on the side. Lush greenery surrounds the property.

Cabin in Leasburg

4.99 out of 5 average rating, 166 reviews

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.

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Guest favourite

The secluded treehouse is elevated among trees, featuring a wooden exterior with a pitched roof. A set of stairs leading to the entrance is visible. Surrounding foliage creates a natural and serene environment, while sunlight filters through the leaves.

Treehouse in Dittmer

4.83 out of 5 average rating, 186 reviews

The Den at Dittmer Hollow

Newly Updated** Enjoy the lovely setting of this romantic spot in nature, with a semi-primitive, modern cozy secluded treehouse in the woods! Explore 10 acres or wind down on the deck before relaxing in the *NEW* hot tub. The cabin inside has a very minimalistic design featuring on the first floor an electric fireplace, air conditioner, table, refrigerator, leather futon couch, kitchenette with a hand crank water pump sink, axe throwing and porta-potty bathroom.

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Superhost

The cabin exterior features natural stone walls and a blue metal roof. Surrounded by large trees, the cabin is set against a grassy backdrop. A gravel driveway leads to the entrance, enhancing the rustic charm of the property.

Cabin in Davisville

4.87 out of 5 average rating, 190 reviews

Peaceful cabin by the Huzzah and Mark Twain Forest

This Cabin is located 15 minutes out of town on a 300 acre cattle farm. If your looking to get away from everyday life and come to the country to relax you have found the perfect place. We are located 6 miles from two river resorts where you can swim or float the river. The amazing Mark Twain Forest is all around us if you enjoy hiking. Build a fire and enjoy your evening on the patio while escaping from your everyday life and enjoy a quiet peaceful retreat.

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Guest favourite

An inviting interior view displays a cozy sleeping area featuring a quilted bedspread. A wood cabinet and a TV are visible, alongside a small dining set. An air conditioning unit provides comfort, while a coffee maker is positioned on a nearby shelf.

Tiny home in Salem

4.91 out of 5 average rating, 230 reviews

Delightful 1 bedroom peaceful tiny house

You won’t forget the peaceful surroundings of this rustic destination. Your stay with us is sure to bring you back to simplicity of life while comfortably cozy and relaxed . While TV and WiFi are available , you will find yourself content with viewing the activities of the surroundings and serene atmosphere. Just minutes away you’ll find exciting selections of activities , excellent dining , and friendly small businesses with a wide selection of interest .

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Top Guest favourite

The cozy bedroom features a large bed with a checkered blanket and natural wood walls. A fan provides airflow, while a window allows soft light to enter. A dark wooden dresser stands nearby, contributing to the rustic charm of the space.

Cabin in St. James

4.99 out of 5 average rating, 230 reviews

Cedar Cabin-Angler’s Catch

Cedar Cabin w/King Bed, Fully Stocked Kitchen, Washer/Dryer, Walk-In Shower, Ramp Access, 2 Decks, Fire Pit, Grill, Free Parking, and 1.3 miles from Beautiful Maramec Spring Park. A trout fisherman’s catch or a couple’s cozy getaway. Close to several Ozark attractions including Maramec Springs Park, Montauk State Park, Current River, Huzzah River, and more. The cabin also has a love seat twin sofa sleeper and is 5 miles from town. Hope to see you soon 😉

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Guest favourite

A cabin-style house features a covered porch with a wooden railing and two chairs. The exterior is a combination of light siding and stone accents. Well-kept greenery surrounds the property, and several trees provide dappled shade.

Farm stay in Potosi

4.87 out of 5 average rating, 175 reviews

Hillside Cottage @Spring Lake Ranch

Cabin style house adjacent to the Mark Twain National Forest. This 5-guest cottage is newly updated with all modern amenities. Take a 3-minute walk to reach the beautiful Spring Lake. The lake is accessible to all guests and offers great fishing, swimming, and kayaking. Love horses? We now offer horseback riding; over 20 miles of trails for you to explore! If you forgot something at home stop by our little country store, we might have it!

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Guest favourite

An aerial view captures a secluded retreat nestled within a dense forest. Lush greenery surrounds a small clearing, where a cabin is partially visible, emphasizing the property's serene and natural setting in the Ozark hills.

Cabin in Steelville

4.97 out of 5 average rating, 34 reviews

20 Acre Cabin Near River - Sleeps 7

Escape to 20 private wooded acres, minutes from the river. Kelly’s Cottage offers a quiet hilltop setting with forest views. Perfect for float trips, you’re 1 mile from Garrison River Outfitters (they offer pickup). Downtown Steelville is 4 miles away. Sleeps up to 7: Queen bedroom downstairs Queen bedroom upstairs Futon (1) Bunk beds (2, best for smaller guests) Pet-friendly (2 pets under 60 lbs, $35 each). Children under 18 stay free.

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