Rosebud Holiday Rentals

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Holiday Rentals in Rosebud

Our top choices for Rosebud holiday rentals

The Pollock Suite is one of our four rooms.

9.8 out of 10, Exceptional, (60)
"Very nice setup and comfortable room. The owners have been incredibly helpful and accomodating."
The price is AU$294
includes taxes & fees
1 Sept - 2 Sept
The Pollock Suite is one of our four rooms.

Get Back to Nature at Three Pine Cabin

9.8 out of 10, Exceptional, (287)
"Host was awesome! Super cozy cabin in a peaceful setting. Great patio for hanging out and grilling outside. We loved our stay!"
Get Back to Nature at Three Pine Cabin

Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!

10.0 out of 10, Exceptional, (134)
"This property is perfect for a quiet , peaceful, stress free getaway. The location on the river bank is fantastic, the cabin itself was super clean and the overall design and decor were wonderful. "
Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!

Glamping with gorgeous sunset views, trolley to all wineries

10.0 out of 10, Exceptional, (3)
"It was a wonderful stay for 5 of us girls going to Herman for a day at the Winery. This location was perfect, just 7 minutes up the road from Downtown Herman. The trolley picked us up with no issue. Very quiet location, perfect for a quick getaway!"
The price is AU$354
includes taxes & fees
1 Sept - 2 Sept
Glamping with gorgeous sunset views, trolley to all wineries

Private Meramec River Frontage!! Cozy Cabin with Amazing views! Available now!!

10.0 out of 10, Exceptional, (19)
"This place was awesome. Will definitely try to stay there again "
Private Meramec River Frontage!! Cozy Cabin with Amazing views! Available now!!

The Monet Suite is one of our four rooms.

10.0 out of 10, Exceptional, (46)
"Beautiful room right next to great night life atmosphere!"
The price is AU$294
includes taxes & fees
1 Sept - 2 Sept
The Monet Suite is one of our four rooms.

Escape to PARADISE on 10 sprawling acres in which to do anything you please!

9.8 out of 10, Exceptional, (28)
"Stay was great and host was extremely helpful, grear views and amenities. Would stay again"
The price is AU$624
includes taxes & fees
9 Sept - 10 Sept
Escape to PARADISE on 10 sprawling acres in which to do anything you please!

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (99)
"Great stay . Perfect for 3 couples. House was exactly as described with a great location. Would 100% stay here again! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

10.0 out of 10, Exceptional, (21)
"We had a very relaxing time and really enjoyed getting to spend some time around the firepit"
The price is AU$226
includes taxes & fees
1 Sept - 2 Sept
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

The Da Vinci Suite is one of our four rooms.

9.8 out of 10, Exceptional, (47)
"Wonderful location nice lean room and close to everything "
The price is AU$294
includes taxes & fees
1 Sept - 2 Sept
The Da Vinci Suite is one of our four rooms.

Newly remodeled home in Historic Hermann Wine Counrtry.

10.0 out of 10, Exceptional, (71)
"Very clean and everything suppled that we needed. The neighborhood was very quiet and nice and the owners were very nice! "
The price is AU$1,204
includes taxes & fees
1 Sept - 2 Sept
Newly remodeled home in Historic Hermann Wine Counrtry.

Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

10.0 out of 10, Exceptional, (217)
"Beautiful house and property. Fantastic view from deck. Enjoyed heated pool, hot tub, tv/gas fireplace in pool area, kayaking on lake, evening fire pit and star gazing. Owner very responsive and easy to contact. "
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

Make some memories at Patten's Landing, our 83-year old restored river cabin!

10.0 out of 10, Exceptional, (19)
"Our stay was phenomenal. They put so much thought into everything to make this a great vacation. Property was amazing and river access put it over top."
Make some memories at Patten's Landing, our 83-year old restored river cabin!

Wine Alley East suite

9.4 out of 10, Exceptional, (71)
"Great place"
The price is AU$326
includes taxes & fees
1 Sept - 2 Sept
Wine Alley East suite

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (49)
"This little house was so cute and the perfect size for 2 couples. Great location! We will definitely stay here again. "
The price is AU$387
includes taxes & fees
9 Sept - 10 Sept
Ash Creek Suite - In Downtown Historic Hermann

Private Logcabin All To Yourself With Lake View

9.8 out of 10, Exceptional, (212)
"Very cool rustic cabin with a neat history."
Private Logcabin All To Yourself With Lake View

Luxury Home in Woods w/ Easy Access to Large Private Gravel Bar on Meramec River

10.0 out of 10, Exceptional, (159)
"We booked this house for a women's retreat and could not have been happier with our stay. The house is beautiful and well functional with two kitchens and 4 bathrooms. With 18 women, no one was even waiting to shower etc. The firepit was lovely and provided us a great place for fellowship. The property managers were responsive and extremely helpful. They were proactive when it was discovered the wifi router was not working. We will definitely keep this at the top of our list for 2026 retreat....
Luxury Home in Woods w/ Easy Access to Large Private Gravel Bar on Meramec River

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (31)
"Was such a cute cottage! We had a wonderful stay and it was just as described! I would definitely stay there again. "
The price is AU$411
includes taxes & fees
1 Sept - 2 Sept
Cozy Riverview Cottage. 5 minute walk to downtown

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

9.8 out of 10, Exceptional, (61)
"It is verry pretty inside, loved the decorations, it had 2 king beds, a great out door area. We loved it because of the location. Its two houses down from the Tin Mill."
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

Goodale Haus

10.0 out of 10, Exceptional, (1)
"overall excellent stay at this property, thank you!"
Goodale Haus
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Rosebud Hotel Reviews

Find out more about Rosebud

Find out more about Rosebud

Everything you need to know about Rosebud holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rosebud holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rosebud holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rosebud holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rosebud. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rosebud holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rosebud holiday rentals we have selected for you start as low as AU$226 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rosebud rentals

At Expedia, we put the best Rosebud holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rosebud rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rosebud holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rosebud. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Rosebud?

Yes, there are holiday rentals close to the most popular sights in Rosebud, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rosebud has to offer?

The House on Wine Alley: This holiday home rental outside of Rosebud offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Rosebud?

Explore the area and family-friendly sights such as Riverside Wildlife Center, or get out into nature at a spot like Meramec Caverns. Cedar Creek Golf Course and Adam Puchta & Son Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Rosebud like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rosebud. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for families.