Rosebud Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rosebud vacation rentals

Spacious Ozarks Family Home - Private Pool & Grill

Spacious Ozarks Family Home - Private Pool & Grill
3.0 star property
Bourbon
The price is CA $502
CA $720 total
includes taxes & fees
Mar 27 - Mar 28
Spacious Ozarks Family Home - Private Pool & Grill

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

Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
Washington
10.0 out of 10, Exceptional, (48 reviews)
"We especially enjoyed the lovely outdoor patios, and the location."
United States
Sallie S.
The price is CA $652
CA $1,205 total
includes taxes & fees
Mar 26 - Mar 27
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!

Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake

Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake
Saint Clair
The price is CA $368
CA $510 total
includes taxes & fees
Mar 26 - Mar 27
Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake

Mid Century Modern Home w/ Private Pool & Lake on 50 Acres

Mid Century Modern Home w/ Private Pool & Lake on 50 Acres
Union
9.8 out of 10, Exceptional, (99 reviews)
"Beautiful place! So much fun for my family of 10. We’re going backDonna great host & easy to communicate with."
United States
Kendelle S.
The price is CA $755
CA $1,462 total
includes taxes & fees
Mar 30 - Mar 31
Mid Century Modern Home w/ Private Pool & Lake on 50 Acres

TJ’s Country Getaway- Dog Friendly

TJ’s Country Getaway- Dog Friendly
Union
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful property, clean and very quiet!"
United States
Lindsay J.
The price is CA $99
CA $222 total
includes taxes & fees
Apr 18 - Apr 19
TJ’s Country Getaway- Dog Friendly

Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
New Haven
8.0 out of 10, Very good, (4 reviews)
"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!"
United States
Judith A.
The price is CA $616
CA $997 total
includes taxes & fees
Mar 26 - Mar 27
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

Charming 3-bedroom house at Heartland Farms in Bourbon,MO

Charming 3-bedroom house at Heartland Farms in Bourbon,MO
Bourbon
10.0 out of 10, Exceptional, (1 review)
"My girlfriends & I loved this property! Fun outdoor activities & great animals! Great house, well decorated & awesome kitchen!! The Locks were great hosts, giving us a dozen of the farm fresh eggs!!"
United States
Marissa Y.
The price is CA $515
CA $627 total
includes taxes & fees
Mar 26 - Mar 27
Charming 3-bedroom house at Heartland Farms in Bourbon,MO

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

Relax in the Ozark woods at a quiet nature retreat with a private walking trail.
Cuba
10.0 out of 10, Exceptional, (25 reviews)
"Cabin was cozy, comfortable and very clean."
United States
Daniel T.
The price is CA $106
CA $207 total
includes taxes & fees
Mar 26 - Mar 27
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.

Lake Cabin near the Bourbeuse River

Lake Cabin near the Bourbeuse River
Leslie
10.0 out of 10, Exceptional, (44 reviews)
"Beautifully relaxing cabin! Can’t wait to stay again and explore more of the area. Perfect get-away!"
United States
Carrie K.
The price is CA $143
CA $217 total
includes taxes & fees
Mar 29 - Mar 30
Lake Cabin near the Bourbeuse River

Moose Lodge

Moose Lodge
Meramec Township
10.0 out of 10, Exceptional, (6 reviews)
"We enjoyed out stay at the Moose Lodge. The house was beautiful with a breath taking view. The private access to the river was a bonus. We will definitely be back!"
United States
Alicia S.
The price is CA $431
CA $770 total
includes taxes & fees
Apr 1 - Apr 2
Moose Lodge

Downtown Hermann Vacation Home Near Wineries!

Downtown Hermann Vacation Home Near Wineries!
3.0 star property
Hermann
10.0 out of 10, Exceptional, (1 review)
"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 CA $663
CA $945 total
includes taxes & fees
Mar 26 - Mar 27
Downtown Hermann Vacation Home Near Wineries!

Fletcher's Village Group Cabin rental near Meramec River.

Fletcher's Village Group Cabin rental near Meramec River.
Leasburg
10.0 out of 10, Exceptional, (6 reviews)
"These three cabins were a perfect fit for our group of eight. The cabins and bathrooms were incredibly clean! We enjoyed having our dinner and morning coffee at the pavilion. A float trip on the Meramec River is only a short drive away. We will definitely consider this for next year’s gathering. "
United States
Joyce H.
The price is CA $458
CA $723 total
includes taxes & fees
Mar 29 - Mar 30
Fletcher's Village Group Cabin rental near Meramec River.

Leasburg Lakehouse vacation home & private stocked lake near Meramec River.

Leasburg Lakehouse vacation home & private stocked lake near Meramec River.
Leasburg
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay. Clean, quiet, good activities for all ages on site. Would definitely return for another stay. "
United States
Sandra M.
The price is CA $520
CA $885 total
includes taxes & fees
Mar 29 - Mar 30
Leasburg Lakehouse vacation home & private stocked lake near Meramec River.

Rustic Cabin Rental with a Wood-Burning Stove near Meramec State Park, Missouri

Rustic Cabin Rental with a Wood-Burning Stove near Meramec State Park, Missouri
Sullivan
The price is CA $183
CA $210 total
includes taxes & fees
Mar 30 - Mar 31
Rustic Cabin Rental with a Wood-Burning Stove near Meramec State Park, Missouri

The Laughing Boar, perfectly located downtown

The Laughing Boar, perfectly located downtown
Hermann
10.0 out of 10, Exceptional, (56 reviews)
"This was a great place to stay! There was plenty room for three families, and the children enjoyed the stay as well! The host did a great job of reaching out as well!"
United States
Joshua S.
The price is CA $549
CA $966 total
includes taxes & fees
Mar 29 - Mar 30
The Laughing Boar, perfectly located downtown

Log Cabin on 10 Acres | Fire Pit & Pets Welcome

Log Cabin on 10 Acres | Fire Pit & Pets Welcome
Bourbon
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful cabin and well appointed "
United States
Christopher F.
The price is CA $218
CA $571 total
includes taxes & fees
Apr 1 - Apr 2
Log Cabin on 10 Acres | Fire Pit & Pets Welcome

Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat

Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat
Bourbon
The price is CA $131
CA $453 total
includes taxes & fees
Mar 29 - Mar 30
Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat

#1 Cabin at Red Oak Valley

#1 Cabin at Red Oak Valley
Canaan Township
10.0 out of 10, Exceptional, (1 review)
"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 CA $247
CA $295 total
includes taxes & fees
Mar 30 - Mar 31
#1 Cabin at Red Oak Valley

Ransom's Retreat Group cabin rental near Meramec River

Ransom's Retreat Group cabin rental near Meramec River
Leasburg
10.0 out of 10, Exceptional, (2 reviews)
"Great property. Very clean. Loved the pavilion. Had a blast!"
United States
Beth T.
The price is CA $409
CA $663 total
includes taxes & fees
Mar 29 - Mar 30
Ransom's Retreat Group cabin rental near Meramec River

Ash Creek Guesthouse - Downtown Historic Hermann

Ash Creek Guesthouse - Downtown Historic Hermann
Hermann
9.8 out of 10, Exceptional, (48 reviews)
"Great!!"
United States
Robert S.
The price is CA $377
CA $654 total
includes taxes & fees
Mar 26 - Mar 27
Ash Creek Guesthouse - Downtown Historic Hermann
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

Find out more about Rosebud

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?

Farmhouse on 6th St: Visitors like this Rosebud vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. 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.

What’s there to see and do in Rosebud?

While exploring the area, visit the sights like Riverside Reptile Ranch, Meramec Caverns, and Adam Puchta & Son Winery. Wenwood Farm Winery and St. Jordan Creek 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.