Holiday houses in Rosebud

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Top-rated holiday rentals in Rosebud

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

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Top Guest favourite
A charming white cottage is set against a backdrop of greenery, featuring dark shutters and a welcoming front porch. A flowering bush with soft pink blooms is situated in the foreground, adding a touch of natural beauty to the scene.
Home in Saint James
5 out of 5 average rating, 109 reviews

Get Cozy in the Country - The Cottage on Luca Hill

A rural stay just 4 miles from the increasingly popular town of St. James. On the farm, you’ll enjoy gorgeous sunsets by the firepit, view the cattle grazing just feet away, and get cozy inside the newly furnished Cottage. Well known for its award winning wineries and dining, STJ also offers various specialty shops and lets not forget the gorgeous Meramec Springs and surrounding rivers. MO S&T and Fort Leonard Wood are just a short drive along I-44 as well. It would be our pleasure to host you!

Top Guest favourite
The bungalow is illuminated by string lights, casting a warm glow around the covered wrap-around porch. The structure's red exterior stands in contrast against the deep blue evening sky, creating a cozy evening ambiance. The surrounding landscape features grass and trees.
Farm stay in Saint James
4.98 out of 5 average rating, 174 reviews

Sunset Valley of St. James- 2 bedroom 1 bath home

This cozy farm cottage sits in the heart of a beautiful farm, yet only 2 miles away from award winning wineries, restaurants, brew house and parks. Newly installed Starlink Satellite for hi-spied wi-fi and internet! Very private and beautifully styled. Minutes from award winning restaurants and wineries. St. James Winery, Sybills Rest, Spencer manor winery. Close to Maramec Spring Park & many rivers for floating. 20 minutes from Missouri S&T & close to Ft Wood. Perfect getaway! 2 queen beds.

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.

Top Guest favourite
The kitchen features a blend of modern and industrial design, highlighted by exposed brick walls and wooden shelving. A double basin sink is situated under a window with black curtains. Kitchen appliances, including a coffee maker and microwave, are visible on the counter.
Home in Owensville
4.97 out of 5 average rating, 119 reviews

The Brick Cottage in Owensville

Enjoy a small town stay in The Brick Cottage! This home is located in the heart of a Owensville right along the highway. The home has been updated with an industrial farmhouse vibe while maintaining its original character & charm. It is the perfect place to stay when in town for weddings, family visits, work travel, or just a getaway. Close to wedding venues & wineries. Visit our small town & stay The Brick Cottage. 30 minutes from Hermann & St. James. 1.5 hours from St. Louis & Columbia.

Top Guest favourite
A well-maintained exterior view showcases a charming building with red brick and a welcoming entrance. Lush greenery and colorful flowering shrubs frame the property, highlighting the manicured lawn and inviting atmosphere of the garden area.
Apartment in Owensville
4.96 out of 5 average rating, 163 reviews

1 Bedroom Hideaway in Historic Downtown Owensville

Steps from the Rock Island Trail! Stay in the F.G. Henneke building in Owensville, MO's historic Hub district. Apartment B is a comfortable 1 bedroom ground floor garden apartment, accessed from your own private off-street entry. 560sf unit completely renovated with new appliances, windows, fixtures, and the restoration of original floors, millwork, and ceilings. The unit retains the building's historical 1907 charm and warmth, with the amenities and comforts we expect in the modern world.

Guest favourite
A private hot tub, designed for four, emits bubbling water under a partially opened cover. The surrounding area includes wooden fencing and a nearby garden chair, creating a secluded space for relaxation.
Cottage in Gasconade
4.91 out of 5 average rating, 308 reviews

1940's River Cottage w/ Hot Tub

Something for everyone! This home is less than 9 mi. from historic Hermann, MO. There you can enjoy several wineries, shops & restaurants. From this property you are just a short walk to the Gasconade River near the MO River. Great boating, fishing & swimming w/ easy boat ramp access & parking. The Union Pacific Railway crosses the river & N. side of town. Gasconade is a small quiet town except for the occasional train or boat going by. At night enjoy stargazing from your private hot tub.

Guest favourite
A spacious wooden porch is featured, with several Adirondack chairs arranged comfortably. Natural wood elements and autumn leaves create a calm setting. Full-length windows offer glimpses of the surroundings, while the latticework adds texture and visual interest to the porch design.
Home in Bonnots Mill
4.94 out of 5 average rating, 353 reviews

Secluded "Heaven": soaker tub, sauna, sunset view

"Heaven" ( 1,512 sq ft, 7 ac) sits on a bluff overlooking the Osage river. An open home with huge full length windows and a sun room. Two porches offer views over the river and to the woods. A soaker tub and sauna are situated in the cabin with a view to the sunset. The cabin is at the end of a secluded forest road. A locked garage is available for small cars. Drive: 15-20 min to Linn for supplies / 30 min to Jeff City / 5 min to public river access. Regretfully no kids under 12 or pets.

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, 167 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.

Top Guest favourite
A spacious green lawn spreads across the foreground, bordered by trees. A two-story farmhouse, renovated and modernized, stands to the left, while a red barn is visible to the right, creating a harmonious rural scene under a clear blue sky.
Farm stay in Owensville
4.99 out of 5 average rating, 115 reviews

Modern Country Farm House with beautiful views

Relax with the whole family or friends at this peaceful place to stay. Located just 6 miles south of Owensville, Mo this newly renovated farm house will provide you the countryside escape you have been looking for with no shortage of amenities. This 2 story farm house was originally constructed in 1888 as a multi family boarding house before the Kreter family purchased it in the 1930’s. In 2021 we made the decision to completely restore the house and bring it to its modern day glory.

Top Guest favourite
The exterior of a round mini house is illuminated by warm light as evening falls. A gentle pink and orange sky serves as a backdrop, highlighting the soft texture of the stucco walls. Nearby, two wooden chairs relax on a grassy area, complementing the serene landscape.
Farm stay in New Haven
4.95 out of 5 average rating, 111 reviews

The Round Room Tower at Moy Mell Farm

Reconnect with nature at this unforgettable escape. Unique, round mini house attached to main house. You will feel like you are far away from the world! We are at the end of a long drive, and in the middle of a small, sustainable farm. We have vegetable market gardens on the premises as well as a variety of farm animals, honeybees, and lots of nature! Even though you will feel isolated and secluded here, we are only minutes away from wineries, a distillery, brewery and art galleries.

Top Guest favourite
The treehouse is illuminated at night, highlighting its modern architecture nestled among trees. Warm lights glow from the windows, contrasting with the dark sky. Surrounding foliage displays vibrant orange hues, adding a serene ambiance to the outdoor setting.
Treehouse in Hermann
4.99 out of 5 average rating, 167 reviews

Out On A Limb Treehouse

A unique Treehouse, 6 miles from Hermann, MO, offers a luxury escape with stunning views and sunsets. Perched on stilts by Daniel Boone Conservation Area, enjoy tranquility, hiking, and wildlife. Relax in a king-size bed beneath skylights, soak in a tub, or unwind in the hot tub and firepit. Just a mile from the Katy Trail, perfect for cycling or relaxing. Explore Hermann’s wineries, shops, and events. Transportation available from Hermann Trolley, Uber & Lyft. Sleeps 2 adults.

Guest favourite
The log cabin is illuminated by warm lights along the porch, casting a welcoming glow against the twilight sky. Surrounding trees frame the cabin, while soft path lights highlight the entryway. The setting evokes a serene atmosphere, ideal for evening relaxation.
Cabin in Bonnots Mill
4.97 out of 5 average rating, 101 reviews

Celestial Log Cabin on the Confluence

Fantastic Eagle Watching! Enchanting 1940's log cabin overlooks the confluence of the Missouri & Osage rivers in charming Bonnots Mill, MO. Close to Columbia, Hermann & Jeff City. Includes master bedroom, open loft, wood-burning hearths, chef's kitchen, clawfoot tub. Double deck overlooking the confluence is a stargazers dream. Secluded, surrounded by nature, find yourself restored after hiking, antiquing, cooking or drinking wine and taking in the beautiful surroundings

Popular amenities for Rosebud holiday rentals