Rosebud Vacation Rentals

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Vacation Rentals in Rosebud

Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!
10.0 out of 10, Exceptional, (87)
"This was a very nice cabin to stay in. The views are spectacular. We had a very nice weekend getaway."
Private River Frontage!!! Beautiful Cabin with Amazing views! Available now!!
Three Rivers Retreat in Steelville, MO Cabin on 20 Acres
10.0 out of 10, Exceptional, (8)
"This cabin was so cute! It had everything we needed and more! Felt like we were at home."
The price is CA $181
CA $363 total
includes taxes & fees
Jun 30 - Jul 1
Three Rivers Retreat in Steelville, MO Cabin on 20 Acres
Leasburg Lakehouse vacation home & private stocked lake near Meramec River.
10.0 out of 10, Exceptional, (2)
"We had a really great time! We fished in the lake played in the creek, and the place was just awesome. It slept all of us just fine and had all kinds of amenities. I will definitely stay here again."
The price is CA $521
CA $798 total
includes taxes & fees
Jun 18 - Jun 19
Leasburg Lakehouse vacation home & private stocked lake near Meramec River.
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Get Back to Nature at Three Pine Cabin
9.8 out of 10, Exceptional, (254)
"We had a great time! Clean, accommodations were impeccable, and scenery was beautiful."
Get Back to Nature at Three Pine Cabin
A Stunning Home, newly constructed & furnished
10.0 out of 10, Exceptional, (44)
"As listed. Perfect place for couples to enjoy time away. Clean and well stocked. Each room was exactly the same allowing all couples to feel equally accommodated. The second smaller house on the property (separate rental that wasn't in our rental/party) is very close but this wasn't an issue for us. We were able to enjoy ourselves and I believe the other rental did too. Ample seating inside and out for all 8 in our party. We paid to use trolley Saturday, but drove ourselves Friday and Saturday....
A Stunning Home, newly constructed & furnished
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
9.6 out of 10, Exceptional, (68)
"Stayed for a bachelorette party and enjoyed the wineries and house aesthetic. Very cute home with so much history. I look forward to staying here again in the future!! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Charming 1913 3 Bedr / 2 Bath / Dutch Brick Haus / Living & Dining / New HVAC
10.0 out of 10, Exceptional, (66)
"What a lovely home! The pictures don't do the place justice, and that's because Paul & Heidi are always diligently looking to improve. Their heart and soul go into this place and it shows! We had a group of five girls total, staying at the Songbird Haus, and it was perfect, we had enough room to hang out in the kitchen, dine at the main table and lounge on the sofas for chit chat. The home is beautiful and we loved how easy it was to walk everywhere in town. The entire stay was just as charming...
Charming 1913 3 Bedr / 2 Bath / Dutch Brick Haus / Living & Dining / New HVAC
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
10.0 out of 10, Exceptional, (8)
"Refreshing retreat for our small church. Relaxing. Everything we needed was there. Open floor plan made time together better. The fireplace and views are amazing."
The price is CA $861
CA $1,435 total
includes taxes & fees
Jun 18 - Jun 19
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
Pet friendly rental near Hermann
9.6 out of 10, Exceptional, (13)
"This delightful home is 20 minutes from downtown Hermann. It was well appointed, had plenty of comfortable beds, and there were lots of amenities. Both showers worked wonderfully. We will stay there again."
The price is CA $251
CA $407 total
includes taxes & fees
Jun 18 - Jun 19
Pet friendly rental near Hermann
Cozy Riverview Cottage. 5 minute walk to downtown
10.0 out of 10, Exceptional, (12)
"The cottage is cozy, comfortable, and full of charm. We felt right at home and Jenna’s customer service was fabulous. Thank you for making our weekend in Hermann perfect!"
The price is CA $275
CA $398 total
includes taxes & fees
Jun 18 - Jun 19
Cozy Riverview Cottage. 5 minute walk to downtown
The Farmhouse Inn: 3 bed, 3.5 whole house rental
10.0 out of 10, Exceptional, (87)
"Perfect house for 3 couples. Huge bonus with a bathroom in each bedroom plus an extra in the living area. Walkable to restaurants and shopping. Trolley picked up at front door. Wonderful stay. Would absolutely book again!"
The Farmhouse Inn: 3 bed, 3.5 whole house rental
Suite #2 - 1 Bed 1 Bath in Downtown Hermann
10.0 out of 10, Exceptional, (57)
"This place was located right in the heart of everything. It was just as described. It was clean, bed was comfortable, room temperature was as you wanted it. We were able to walk to everything. I would stay here again."
Suite #2 - 1 Bed 1 Bath in Downtown Hermann
Suite on Schiller
9.8 out of 10, Exceptional, (86)
"Wonderful trip "
Suite on Schiller
Ash Creek Suite - In Downtown Historic Hermann
9.4 out of 10, Exceptional, (36)
"It was very nice and had a lot to do in walking distance."
The price is CA $275
CA $471 total
includes taxes & fees
Jun 18 - Jun 19
Ash Creek Suite - In Downtown Historic Hermann
Brick Bungalow
10.0 out of 10, Exceptional, (37)
"Great location and clean."
Brick Bungalow
Seclusion in a beautiful setting where your dog can run free!
9.8 out of 10, Exceptional, (213)
"We we’re doing some traveling and decided we wanted to extend our trip a little for us. We’ve stayed here 2 other times, and the peace, quiet, and seclusion are always just what the doctor ordered. We lucked out, the weather was amazing and we just stuck around enjoying the views."
Seclusion in a beautiful setting where your dog can run free!
Wine Alley East suite
9.2 out of 10, Wonderful, (45)
"Location was very handy - had everything we needed! Would definitely stay here again!"
The price is CA $199
CA $288 total
includes taxes & fees
Jun 18 - Jun 19
Wine Alley East suite
A Charming Home newly remodeled and furnished
10.0 out of 10, Exceptional, (45)
"Very nice, well maintained and homey."
A Charming Home newly remodeled and furnished
Private Logcabin All To Yourself With Lake View
9.8 out of 10, Exceptional, (185)
"Beautiful cabin and grounds. Best stocked kitchen I've ever seen. So peaceful and private."
Private Logcabin All To Yourself With Lake View
Newly built LOG Cabin-Float, Golf, Hike, Hunt, Fish, visit a winery...Relax!
10.0 out of 10, Exceptional, (16)
"Hostess was very accommodating and quickly responded to my requests for info or needs. Beautiful property and cabin. Grandkids had a great time during our short stay in Cuba (was there for a wedding). The washer was not working just prior to our arrival and the host was amazingly accommodating and willing to work with us. Great experience! You will not be disappointed!"
Newly built LOG Cabin-Float, Golf, Hike, Hunt, Fish, visit a winery...Relax!
Don't see what you're looking for?
See all available properties in Rosebud
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.

Other types of properties in Rosebud you may be interested in

Pinemark Inn & Suites
2.0 star property
9.4 out of 10, Exceptional, (1003)
"ok"
The price is CA $192
CA $210 total
includes taxes & fees
Jun 18 - Jun 19
Pinemark Inn & Suites
Super 8 by Wyndham Cuba
2.0 star property
8.8 out of 10, Excellent, (824)
"Great clean stay "
The price is CA $99
CA $113 total
includes taxes & fees
Jun 24 - Jun 25
Super 8 by Wyndham Cuba
Baymont by Wyndham Sullivan
2.5 star property
7.8 out of 10, Good, (1003)
"Stayed here for a weekend getaway and the kids loved the pool/hot tub for sure. Room was nice and adequate for our needs. Looks like they are trying to update some areas which is good and needed. Our room was clean but a bit dated. Comfy beds and big tv after playing in the pool!"
The price is CA $136
CA $148 total
includes taxes & fees
Jul 7 - Jul 8
Baymont by Wyndham Sullivan
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Rosebud. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Leasburg Lakehouse vacation home & private stocked lake near Meramec River.: Visitors like this Rosebud vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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. Sullivan Country Club 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.

Recent reviews of Rosebud properties
Expedia verified reviews