Holiday Rentals in Rosebud

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Rosebud

Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!

10.0 out of 10, Exceptional, (38)
"The perfect place for our family reunion. Something for everyone….pool, basketball hoop, swing set, hot tub, fire pit and a huge yard for the kiddos to run around. "
The price is €763
includes taxes & fees
6 Oct - 7 Oct
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!

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

10.0 out of 10, Exceptional, (22)
"We had a very relaxing time and really enjoyed getting to spend some time around the firepit"
The price is €135
includes taxes & fees
5 Oct - 6 Oct
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

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

9.8 out of 10, Exceptional, (29)
"Stay was great and host was extremely helpful, grear views and amenities. Would stay again"
The price is €285
includes taxes & fees
23 Oct - 24 Oct
Escape to PARADISE on 10 sprawling acres in which to do anything you please!

Suite on Schiller

9.8 out of 10, Exceptional, (111)
"Great place to stay and location was perfect."
Suite on Schiller

The Van Gogh Suites is one of our four rooms.

9.6 out of 10, Exceptional, (35)
"This was our second time to say at the Artist Suites. We enjoy staying here because each suite is unique and we like the downtown location. Next time we visit Hermann we will once again stay here "
The price is €167
includes taxes & fees
2 Nov - 3 Nov
The Van Gogh Suites is one of our four rooms.

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

10.0 out of 10, Exceptional, (140)
"Beautiful property and cozy cabin. We had a wonderful stay and would definitely stay again! "
Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!

Cozy Cabin in the woods near charming Hermann

Cozy Cabin in the woods near charming Hermann

Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

10.0 out of 10, Exceptional, (147)
"We stay here each year for a bike race weekend. We really enjoy the space and the location!!"
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (49)
"Great location in a lovely town."
The price is €304
includes taxes & fees
5 Oct - 6 Oct
Ash Creek Suite - In Downtown Historic Hermann

Private Logcabin All To Yourself With Lake View

9.8 out of 10, Exceptional, (214)
"Very cool rustic cabin with a neat history."
Private Logcabin All To Yourself With Lake View

The Pollock Suite is one of our four rooms.

9.8 out of 10, Exceptional, (62)
"We had a really nice stay and would definitely book again."
The price is €167
includes taxes & fees
2 Nov - 3 Nov
The Pollock Suite is one of our four rooms.

The Da Vinci Suite is one of our four rooms.

9.8 out of 10, Exceptional, (50)
"Great place and location, very clean."
The price is €167
includes taxes & fees
2 Nov - 3 Nov
The Da Vinci Suite is one of our four rooms.

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (33)
"We had a great stay at Autzie’s and was the perfect setting for our 20th wedding anniversary getaway. Thanks"
The price is €232
includes taxes & fees
5 Oct - 6 Oct
Cozy Riverview Cottage. 5 minute walk to downtown

Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

8.8 out of 10, Excellent, (3)
"This is definitely not your conventional vacation place to stay - a working farm, log cabin portions, modern kitchen appliances hidden in plain sight behind old farmhouse cabinets, eclectic decor that you can spend hours browsing and looking at so many unique items. But it was exactly what I was looking for and everything turned out very well. Thank you!"
The price is €594
includes taxes & fees
5 Oct - 6 Oct
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

Three Rivers Retreat in Steelville, MO. 2 Bedroom Cabin on 20 Acres

9.2 out of 10, Wonderful, (36)
"We will be back. No complaints! "
The price is €243
includes taxes & fees
6 Oct - 7 Oct
Three Rivers Retreat in Steelville, MO. 2 Bedroom Cabin on 20 Acres

Glamping with gorgeous sunset views, trolley to all wineries

9.4 out of 10, Exceptional, (6)
"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 €200
includes taxes & fees
5 Oct - 6 Oct
Glamping with gorgeous sunset views, trolley to all wineries

Mid Century Modern Home w/ Private Pool & Lake on 50 Acres

9.8 out of 10, Exceptional, (99)
"Beautiful place! So much fun for my family of 10. We’re going backDonna great host & easy to communicate with."
The price is €1,168
includes taxes & fees
14 Oct - 15 Oct
Mid Century Modern Home w/ Private Pool & Lake on 50 Acres

Newly remodeled home in Historic Hermann Wine Counrtry.

10.0 out of 10, Exceptional, (72)
"Great town to visit and the house was perfect for the trip."
The price is €735
includes taxes & fees
3 Nov - 4 Nov
Newly remodeled home in Historic Hermann Wine Counrtry.

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!!

Get Back to Nature at Three Pine Cabin

9.8 out of 10, Exceptional, (289)
"It was great place to stay for the family float trip! Thank you!"
Get Back to Nature at Three Pine Cabin
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 favorite 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 depends 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 €135 per night. Entering your travel dates in the search wizard you might find 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?

Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!: This holiday home rental outside of Rosebud is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Rosebud?

While exploring the area, visit the sights like Cedar Creek Golf Course, Meramec Caverns and Adam Puchta & Son Winery. Wenwood Farm Winery and Bommarito Estate Almond Tree 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.