Rosebud Holiday Rentals

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Holiday Rentals in Rosebud

TJ’s Country Getaway- Dog Friendly

Union
10.0 out of 10, Exceptional, (45)
"We loved our stay it was very comfortable and highly recommend staying here."
United States
Heath S.
The price is NZ$242
includes taxes & fees
2 Dec - 3 Dec
TJ’s Country Getaway- Dog Friendly

RGM Farms Guesthouse, rustic yet comfy with kitchenette.

Bourbon
9.8 out of 10, Exceptional, (25)
"Cute quaint place, easily accessible to meremec caverns and state Park. Kitchen had everything needed and check in and out was simple. Will definitely stay here again "
United States
Sarah M.
The price is NZ$223
includes taxes & fees
2 Dec - 3 Dec
RGM Farms Guesthouse, rustic yet comfy with kitchenette.

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

Cuba
10.0 out of 10, Exceptional, (24)
"Nice, clean space with just enough room for a couple guys. Great patio and scenery."
United States
stirFRYE32 F.
The price is NZ$266
includes taxes & fees
12 Nov - 13 Nov
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

Lake Cabin near the Bourbeuse River

Leslie
10.0 out of 10, Exceptional, (42)
"I absolutely loved the peaceful, beautiful scenery. The house was extraordinarily clean and the log stove with already cut wood was a wonderful addition. Fantastic hosts! "
United States
Stacey
The price is NZ$291
includes taxes & fees
18 Nov - 19 Nov
Lake Cabin near the Bourbeuse River

New Camper with a Hot Tub and Pool: Great For Families or a Romantic Weekend.

Union
10.0 out of 10, Exceptional, (1)
"We loved our visit! The kids loved the pool, camper, animals and property. Justin and Kati's hospitality was exceptional! Camper was super clean and easy to utilize. We will definitely be back! "
United States
Jennifer M.
The price is NZ$419
includes taxes & fees
18 Nov - 19 Nov
New Camper with a Hot Tub and Pool: Great For Families or a Romantic Weekend.

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

Steelville
9.2 out of 10, Wonderful, (38)
"Small but cozy. We liked it. "
United States
Craig S.
The price is NZ$491
includes taxes & fees
12 Nov - 13 Nov
Three Rivers Retreat in Steelville, MO. 2 Bedroom Cabin on 20 Acres

Firepit, Pet-Friendly, 10 Private Acres - Modern Log Cabin

Bourbon
10.0 out of 10, Exceptional, (36)
"Nice relaxingnweekendb"
United States
Andrew J.
The price is NZ$776
includes taxes & fees
10 Dec - 11 Dec
Firepit, Pet-Friendly, 10 Private Acres - Modern Log Cabin

Country Cabin with Jacuzzi Tub Near Blue Springs Ranch

Bourbon
10.0 out of 10, Exceptional, (11)
"Very nice cabin and area"
United States
Charles
The price is NZ$327
includes taxes & fees
11 Dec - 12 Dec
Country Cabin with Jacuzzi Tub Near Blue Springs Ranch

Primitive Campsites with water spigot, toilets, and wifi!

Bourbon
The price is NZ$109
includes taxes & fees
12 Nov - 13 Nov
Primitive Campsites with water spigot, toilets, and wifi!

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

Leasburg
9.8 out of 10, Exceptional, (30)
"We had a great night at the house, the fire pit area was really great and we loved the big kitchen/ living room. "
United States
Cindy S.
The price is NZ$645
includes taxes & fees
12 Nov - 13 Nov
Escape to PARADISE on 10 sprawling acres in which to do anything you please!

#1 Cabin at Red Oak Valley

Canaan Township
10.0 out of 10, Exceptional, (1)
"Although small, the place was super clean, comfortable and cozy. Would highly recommend. My only suggestion would be to add signs when you come through the entrance. We had no idea which way to go and cell service was spotty so it took a minute before we could call the property manager."
United States
Jessica P.
The price is NZ$383
includes taxes & fees
12 Nov - 13 Nov
#1 Cabin at Red Oak Valley

Glamping with gorgeous sunset views, trolley to all wineries

Berger
9.6 out of 10, Exceptional, (9)
"Property was nice. Close enough to downtown Hermann but far enough away from the noise."
United States
Amanda O.
The price is NZ$408
includes taxes & fees
13 Nov - 14 Nov
Glamping with gorgeous sunset views, trolley to all wineries

Back Door Guest Suite, Zia My Retreat

New Haven
10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay! We loved how creative the layout and decorations were. The place has everything you’d need and expect to find. The bed is super comfy! The host was very responsive. The cafe next door has excellent sandwiches and coffee (but it’s closed on Sundays). Don’t expect much from the “river walk”. It’s really just a sidewalk not more than a block and a half long. New Haven is close to Hermann, so we went there and rented e-bikes and rode the Katy Trail. Super fun! If you’re...
United States
Christine P.
Back Door Guest Suite, Zia My Retreat

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

Washington
10.0 out of 10, Exceptional, (43)
"Home was very nice, had a great location and manager was fantastic to work with. "
United States
Pat R.
The price is NZ$1,507
includes taxes & fees
8 Dec - 9 Dec
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!

Charming 2-bedroom house in fabulous downtown Hermann

Hermann
10.0 out of 10, Exceptional, (2)
"Charming historical cottage near downtown venues!"
United States
Sarah M.
The price is NZ$471
includes taxes & fees
10 Dec - 11 Dec
Charming 2-bedroom house in fabulous downtown Hermann

Downtown Hermann Vacation Home Near Wineries!

3.0 star property
Hermann
10.0 out of 10, Exceptional, (1)
"This is a very cute little house on the end of a quiet street. It's within easy walking distance of all the shops, restaurants, wineries, distilleries, and bars between 1st Street and 5th Street. If you don't mind a longer, hillier walk you could also go further south to City Park or to Stone Hill winery. But there's also easy transportation on the Trolley or local ride services. We were happy to find there were more beds than pictured (3 queen size downstairs between 2 bedrooms, and 2 queens...
United States
Tara
The price is NZ$1,281
includes taxes & fees
13 Nov - 14 Nov
Downtown Hermann Vacation Home Near Wineries!

Gipfel Suite - Himmel Haus Bed & Breakfast

Hermann
10.0 out of 10, Exceptional, (111)
"The room was very nice. Renee thought of everything we could possibly need. The homemade hot breakfast was excellent. Thank you!"
United States
Stacey W.
The price is NZ$297
includes taxes & fees
12 Nov - 13 Nov
Gipfel Suite - Himmel Haus Bed & Breakfast

The Monet Suite is one of our four rooms.

Hermann
10.0 out of 10, Exceptional, (54)
"The room was excellent and has everything we needed!"
United States
Bill D.
The price is NZ$363
includes taxes & fees
12 Nov - 13 Nov
The Monet Suite is one of our four rooms.

Ash Creek Suite - In Downtown Historic Hermann

Hermann
9.4 out of 10, Exceptional, (51)
"Good location and accommodations"
United States
Angie O.
The price is NZ$447
includes taxes & fees
3 Dec - 4 Dec
Ash Creek Suite - In Downtown Historic Hermann

Cozy Riverview Cottage. 5 minute walk to downtown

Hermann
10.0 out of 10, Exceptional, (41)
"Was such a cute cottage! We had a wonderful stay and it was just as described! I would definitely stay there again. "
United States
sherri s.
The price is NZ$368
includes taxes & fees
12 Nov - 13 Nov
Cozy Riverview Cottage. 5 minute walk to downtown
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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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 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 NZ$266 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?

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!: This holiday home rental outside of Rosebud is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.