Rosebud Vacation Rentals

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Vacation Rentals in Rosebud

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 CA $150
CA $263 total
includes taxes & fees
Sep 4 - Sep 5
The Pollock Suite is one of our four rooms.

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!!

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

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 CA $207
CA $316 total
includes taxes & fees
Sep 4 - Sep 5
Glamping with gorgeous sunset views, trolley to all wineries

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 CA $413
CA $550 total
includes taxes & fees
Sep 16 - Sep 17
Escape to PARADISE on 10 sprawling acres in which to do anything you please!

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 CA $150
CA $263 total
includes taxes & fees
Sep 4 - Sep 5
The Monet Suite is one of our four rooms.

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 CA $100
CA $201 total
includes taxes & fees
Sep 8 - Sep 9
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

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 CA $248
CA $366 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Riverview Cottage. 5 minute walk to downtown

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!!

Brick Bungalow

10.0 out of 10, Exceptional, (58)
"Highly recommend!"
Brick Bungalow

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 CA $172
CA $346 total
includes taxes & fees
Sep 18 - Sep 19
Ash Creek Suite - In Downtown Historic Hermann

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

10.0 out of 10, Exceptional, (218)
"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

The Black Magnolia - downtown with a charming patio to enjoy

10.0 out of 10, Exceptional, (2)
"Had a great stay!"
The Black Magnolia - downtown with a charming patio to enjoy

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 CA $617
CA $942 total
includes taxes & fees
Sep 4 - Sep 5
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

The Van Gogh Suites is one of our four rooms.

9.6 out of 10, Exceptional, (33)
"Right in the middle of all the action. Loved the neighborhood!"
The price is CA $150
CA $263 total
includes taxes & fees
Sep 4 - Sep 5
The Van Gogh Suites is one of our four rooms.

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

10.0 out of 10, Exceptional, (20)
"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!

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

10.0 out of 10, Exceptional, (21)
"This place was awesome. Will definitely try to stay there again "
Private Meramec River Frontage!! Cozy Cabin with Amazing views! Available now!!

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

Country Cabin with Jacuzzi Tub Near Blue Springs Ranch

9.8 out of 10, Exceptional, (10)
"Very nice cabin and area"
The price is CA $248
CA $300 total
includes taxes & fees
Sep 14 - Sep 15
Country Cabin with Jacuzzi Tub Near Blue Springs Ranch

Gipfel Suite - Himmel Haus Bed & Breakfast

10.0 out of 10, Exceptional, (106)
"We booked this last minute as a short birthday trip away from home. It was wonderful! So quiet, perfect suite (clean, great mattress, wonderful set up) and excellent breakfast! AND super parking situation! Thanks Renee for a wonderful stay."
The price is CA $136
CA $231 total
includes taxes & fees
Sep 22 - Sep 23
Gipfel Suite - Himmel Haus Bed & Breakfast
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rosebud vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rosebud vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rosebud vacation rentals we have selected for you start as low as CA $100 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 vacation 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 vacation.

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 vacation rentals in Rosebud?

Yes, we offer vacation rentals close to the most popular points of interest in Rosebud, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Rosebud has to offer?

The House on Wine Alley: Visitors like this Rosebud vacation home rental. It 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 you can cook with friends or family. Make the most of the selection 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 larger area.

What’s a vacation rental in Rosebud like?

A vacation rental is a private property where you can stay for a long or short time in Rosebud. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family getaway.