Holiday Rentals in Rosebud

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Holiday Rentals in Rosebud

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 €279
includes taxes & fees
24 Aug - 25 Aug
The House on Wine Alley

The Da Vinci Suite is one of our four rooms.

9.8 out of 10, Exceptional, (47)
"The room was nice, close to everything. "
The price is €169
includes taxes & fees
18 Aug - 19 Aug
The Da Vinci Suite is one of our four rooms.

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 €129
includes taxes & fees
18 Aug - 19 Aug
The Pollock Suite is one of our four rooms.

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (30)
"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 €233
includes taxes & fees
24 Aug - 25 Aug
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, (28)
"Stay was great and host was extremely helpful, grear views and amenities. Would stay again"
The price is €286
includes taxes & fees
25 Aug - 26 Aug
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, (133)
"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, (284)
"Even with the rain it was an amazingly beautiful place! Totally peaceful mornings watching the baby birds chirping for Mama. All around great hideaway for those looking to get away from everyday hussle! "
Get Back to Nature at Three Pine Cabin

The Van Gogh Suites is one of our four rooms.

9.6 out of 10, Exceptional, (33)
"We had a quick overnight stay in Hermann. The room was perfect for our needs! This is our second time staying, been great both times. Thanks!"
The price is €168
includes taxes & fees
24 Aug - 25 Aug
The Van Gogh Suites is one of our four rooms.

Wine Alley East suite

9.4 out of 10, Exceptional, (70)
"Great location "
The price is €186
includes taxes & fees
18 Aug - 19 Aug
Wine Alley East suite

Gipfel Suite - Himmel Haus Bed & Breakfast

10.0 out of 10, Exceptional, (104)
"1st time in Hermann and loved our stay. Very clean and hospitable and peaceful "
The price is €147
includes taxes & fees
18 Aug - 19 Aug
Gipfel Suite - Himmel Haus Bed & Breakfast

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 €682
includes taxes & fees
17 Aug - 18 Aug
Newly remodeled home in Historic Hermann Wine Counrtry.

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

10.0 out of 10, Exceptional, (19)
"We had a very relaxing time and really enjoyed getting to spend some time around the firepit"
The price is €124
includes taxes & fees
17 Aug - 18 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, (17)
"My husband and I came for a quiet week away, and had a wonderful relaxing time! I could look out at the river all day from the living room windows. The host was very accommodating and helpful with our questions. Highly recommend, and I will be back!"
Private Meramec River Frontage!! Cozy Cabin with Amazing views! Available now!!

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 €207
includes taxes & fees
17 Aug - 18 Aug
Ash Creek Suite - In Downtown Historic Hermann

Brick Bungalow

10.0 out of 10, Exceptional, (57)
"Highly recommend!"
Brick Bungalow

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

10.0 out of 10, Exceptional, (215)
"Had a wonderful time, it is an amazing place to stay"
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

Lake Cabin near the Bourbeuse River

10.0 out of 10, Exceptional, (36)
"This is the perfect place! Can’t say enough good things about it! "
The price is €144
includes taxes & fees
27 Aug - 28 Aug
Lake Cabin near the Bourbeuse River

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

Spacious 2 bed, Hot tub, beautiful back deck overlooking Meramec River

9.0 out of 10, Wonderful, (8)
"My family and I stayed here over Thanksgiving. It was the perfect escape from the hustle and bustle."
Spacious 2 bed, Hot tub, beautiful back deck overlooking Meramec River

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 €201
includes taxes & fees
24 Aug - 25 Aug
Glamping with gorgeous sunset views, trolley to all wineries
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

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.