Plan your trip

Rosebud Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

    Sign in

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, December 14–15, 2026

    View in a map

    Our top choices for Rosebud vacation rentals

    1. Lake Cabin near the Bourbeuse River

    A rural landscape with a pond, a small tree, a barn, and a white house.

    2. Cozy Cabin in the woods near charming Hermann

    A room with a wooden wall, a television mounted above a wooden table with chairs, a trash bin, and a door with a window.

    3. Rock Island Hideaway Classic Cozy Apartment in Downtown Owensville Missouri

    Interior

    4. RGM Farms Guesthouse, rural tranquil setting for family & friends to enjoy.

    A covered outdoor area with a wooden structure, surrounded by trees.

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

    A modern house with a wooden exterior, a sloped roof, and a fenced backyard.

    6. #1 Cabin at Red Oak Valley

    A spacious living area with a ceiling fan, a kitchen with wooden cabinets, and a dining area with a table and chairs.

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

    A wooden bench with a cushion labeled "Relax" on a porch overlooking a forest.

    8. Primitive Campsites with water spigot, toilets, and wifi!

    A welcome sign for RGM Farms with a quote and a biblical reference.

    9. The Cottage

    A wooden bridge leading to a two-story house with multiple windows and a covered porch.

    10. Cozy Cabin near Owensville, Missouri - Perfect for a Glamping Getaway with Your Significant Other

    A room with a grey sofa, a grey armchair, a ceiling fan, and a large window.

    11. Romantic Glamping Getaway Perfect for Quality Time with Your Partner: Cute Tiny House near Owensville, Missouri

    Interior

    12. Back Door Guest Suite, Zia My Retreat

    A cozy living room with a high ceiling, a rocking chair, and a fireplace.

    13. Cozy 2-bedroom house in Cuba, MO.

    A small storage closet with a vacuum cleaner, a metal rack, and storage boxes.

    14. Rustic Cabin Rental near Meramec State Park, Missouri

    Outdoor dining

    15. Zinfandel Room - Old Vine

    A covered patio area with a glass table and chairs, a barbecue grill, and a seating area with sofas and chairs.

    16. Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

    A modern building with a metal exterior, large windows, and outdoor air conditioning units.

    17. Wine Alley West Suite

    A compact kitchen with a wooden countertop and stools, a dark sofa, and two armchairs in a living area with hardwood flooring.

    18. Fire Pit, 10 private Acres | Pets Welcome

    A log cabin with a wooden deck, wicker chairs, and a covered porch.

    19. Country Cabin with Jacuzzi Tub and Meramec River Access and Pets welcome!

    A covered patio with two red lounge chairs and a wooden table.

    20. Gipfel Suite - Himmel Haus Bed & Breakfast

    An outdoor patio with a pergola, wicker furniture, and a view of the landscape.

    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.

    View all properties

    Find vacation rentals that suit your style

    Cabins

    Aparthotels

    Apartments

    Cottages

    Condos

    Top Rosebud Hotel Reviews

    Comfort Inn Sullivan

    A Comfort Inn hotel with a modern design, featuring a covered entrance and a clear sky in the background.

    Super 8 by Wyndham Cuba

    A hotel room with a red carpet, a sofa set, a desk with a lamp, and a large window with curtains.

    Motel 6 Sullivan, MO

    A hotel room with a bed, two bedside tables, a ceiling fan, and two wall-mounted lamps.

    Hermann Crown Suites

    A restaurant with brick walls, wooden tables, and chairs.

    Americas Best Value Inn Sullivan

    A hotel room with two beds, a desk, a chair, a lamp, and a painting on the wall.

    Days Inn & Suites by Wyndham Cuba

    A hotel room with a large bed, two bedside lamps, a nightstand, and a wall with three framed pictures.

    Find out more about Rosebud

    Everything you need to know about Rosebud vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rosebud vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Rosebud vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Rosebud vacation rentals we have selected for you start as low as CA $55 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 vacation 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 vacation.

    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 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?

    Cozy Riverview Cottage. 5 minute walk to downtown: Visitors like this Rosebud vacation home rental. It is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

    What’s there to see and do in Rosebud?

    While exploring the area, visit the sights like Meramec Caverns, Adam Puchta & Son Winery, and Bommarito Estate Almond Tree Winery. Martin Brothers Winery and Cedar Creek Golf Course 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.