Search Holiday Rentals in Rosebud

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Rosebud

The Pollock Suite is one of our four rooms.

9.8 out of 10, Exceptional, (59)
"Very nice setup and comfortable room. The owners have been incredibly helpful and accomodating."
The price is £146
includes taxes & fees
25 Aug - 26 Aug
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 £174
includes taxes & fees
25 Aug - 26 Aug
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 £248
includes taxes & fees
2 Sept - 3 Sept
Escape to PARADISE on 10 sprawling acres in which to do anything you please!

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

10.0 out of 10, Exceptional, (20)
"We had a very relaxing time and really enjoyed getting to spend some time around the firepit"
The price is £111
includes taxes & fees
26 Aug - 27 Aug
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

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!!

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

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 £146
includes taxes & fees
25 Aug - 26 Aug
The Monet Suite is one of our four rooms.

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!!

The House on Wine Alley

9.0 out of 10, Wonderful, (47)
"Great place to stay in the heart of Hermann! Definitely recommend!"
The price is £243
includes taxes & fees
25 Aug - 26 Aug
The House on Wine Alley

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

10.0 out of 10, Exceptional, (216)
"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 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 £146
includes taxes & fees
25 Aug - 26 Aug
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 £588
includes taxes & fees
25 Aug - 26 Aug
Newly remodeled home in Historic Hermann Wine Counrtry.

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!

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

10.0 out of 10, Exceptional, (141)
"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

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

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 £181
includes taxes & fees
25 Aug - 26 Aug
Ash Creek Suite - In Downtown Historic Hermann

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 £519
includes taxes & fees
25 Aug - 26 Aug
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

Wine Alley East suite

9.4 out of 10, Exceptional, (71)
"Great place"
The price is £160
includes taxes & fees
25 Aug - 26 Aug
Wine Alley East suite
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

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 Artists Suites, Jackson Pollock Suite: This holiday home rental outside of Rosebud is located in the city centre, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a fridge and a coffee maker can make your holiday run smoothly.

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.