Rosebud Holiday Rentals

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Holiday Rentals in Rosebud

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
9.8 out of 10, Exceptional, (64)
"We loved our stay! The inn was in a great and convenient location to shops, wineries, and restaurants. The house was cute, comfortable and COOL during the heat wave of late July. The hosts were quick to respond to any questions we had."
United States
Karen H.
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Cozy Riverview Cottage. 5 minute walk to downtown
10.0 out of 10, Exceptional, (37)
"We absolutely loved our stay at Autzie’s. The cottage, outdoor space and location can’t be beat. We can’t wait to come back; we’ll definitely stay here again. "
United States
Michelle W.
The price is AU$409
includes taxes & fees
9 Nov - 10 Nov
Cozy Riverview Cottage. 5 minute walk to downtown
Escape to PARADISE on 10 sprawling acres in which to do anything you please!
9.8 out of 10, Exceptional, (29)
"We needed a place to land after a long day of travel. It was just what we needed. Nice big open space for our group to eat and hang out. The pool was refreshing and the owners were a pleasure to work with. We would definitely stay there again if we are in the area!"
United States
I am B.
The price is AU$513
includes taxes & fees
9 Nov - 10 Nov
Escape to PARADISE on 10 sprawling acres in which to do anything you please!
Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!
10.0 out of 10, Exceptional, (143)
"Beautiful property and cozy cabin. We had a wonderful stay and would definitely stay again! "
United States
Sarah W.
Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!
Wine Alley East suite
9.4 out of 10, Exceptional, (74)
"Great location clean safe "
United States
Toshmon
The price is AU$324
includes taxes & fees
12 Nov - 13 Nov
Wine Alley East suite
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.
10.0 out of 10, Exceptional, (24)
"We had a very relaxing time and really enjoyed getting to spend some time around the firepit"
United States
Hannah N.
The price is AU$233
includes taxes & fees
2 Nov - 3 Nov
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
10.0 out of 10, Exceptional, (149)
"We stay here each year for a bike race weekend. We really enjoy the space and the location!!"
United States
Craig W.
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
10.0 out of 10, Exceptional, (42)
"Very spacious home indoors and out! Loved the decor, easy access to the pool, great location for us! The hosts were very friendly, understanding to our needs, and easy to work with. We will stay here again!"
United States
Cindy C.
The price is AU$1,311
includes taxes & fees
12 Nov - 13 Nov
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
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!"
United States
Judith A.
The price is AU$1,054
includes taxes & fees
27 Nov - 28 Nov
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
Cozy Cabin in the woods near charming Hermann
10.0 out of 10, Exceptional, (2)
"Very secluded and cozy. Perfect for a couples getaway "
United States
Jeremy R.
Cozy Cabin in the woods near charming Hermann
Private Guest House-Hermann MO
10.0 out of 10, Exceptional, (38)
"We were very happy with our stay. Great location for walking to the places we wanted to go shopping eating and coffee. Bed was comfortable. We will visit again. "
United States
Jackie A.
Private Guest House-Hermann MO
Glamping with gorgeous sunset views, trolley to all wineries
9.6 out of 10, Exceptional, (8)
"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!"
United States
Belen A.
The price is AU$353
includes taxes & fees
9 Nov - 10 Nov
Glamping with gorgeous sunset views, trolley to all wineries
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
9.6 out of 10, Exceptional, (101)
"Check was simple. Area was great. Wifi worked perfectly."
United States
Raymond W.
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Newly remodeled home in Historic Hermann Wine Counrtry.
10.0 out of 10, Exceptional, (75)
"Great town to visit and the house was perfect for the trip."
United States
Jake B.
The price is AU$1,190
includes taxes & fees
12 Nov - 13 Nov
Newly remodeled home in Historic Hermann Wine Counrtry.
Suite on Schiller
9.8 out of 10, Exceptional, (114)
"Great little place with a great location very comfortable"
United States
Barry Z.
Suite on Schiller
Fall Nights, Firepit, 10 Acres - Perfect Getaway
10.0 out of 10, Exceptional, (36)
"Excellent location and beautiful cabin. Would definitely stay there again."
United States
Jackie P.
The price is AU$571
includes taxes & fees
11 Nov - 12 Nov
Fall Nights, Firepit, 10 Acres - Perfect Getaway
A nice view of the woods awaits you from the countryside kitchen window and deck
10.0 out of 10, Exceptional, (77)
"Great place to stay. This was our 9th year!Quite and river access in minutes."
United States
Tina L.
A nice view of the woods awaits you from the countryside kitchen window and deck
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."
United States
Kendelle S.
The price is AU$2,057
includes taxes & fees
30 Oct - 31 Oct
Mid Century Modern Home w/ Private Pool & Lake on 50 Acres
Private Logcabin All To Yourself With Lake View
9.8 out of 10, Exceptional, (215)
"We loved it and plan on returning "
United States
Jesse S.
Private Logcabin All To Yourself With Lake View
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace
10.0 out of 10, Exceptional, (221)
"Such a great place to connect with family or friends. "
United States
Jon H.
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace
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

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$233 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?

Cozy Riverview Cottage. 5 minute walk to downtown: This holiday home rental outside of Rosebud is equipped with a patio, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.