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Rosebud Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Rosebud vacation rentals

Terrace/patio

1. Lake Cabin near the Bourbeuse River

Lake Cabin near the Bourbeuse River
Leslie
10.0 out of 10, Exceptional, (56 reviews)
"It was a perfect restful stay!"
United States
Sheryl R.
The price is ￥16,649
￥25,294 total
includes taxes & fees
Sep 7 - Sep 8
Lake Cabin near the Bourbeuse River
Exterior

2. The Paddock House at Dark Horse Farms. 3Bd 2bath Sleeps 12 nestled on 70 acres

The Paddock House at Dark Horse Farms. 3Bd 2bath Sleeps 12 nestled on 70 acres
Owensville
10.0 out of 10, Exceptional, (2 reviews)
"Wished we could stay longer!"
United States
Shane B.
The price is ￥27,375
￥49,291 total
includes taxes & fees
Sep 1 - Sep 2
The Paddock House at Dark Horse Farms. 3Bd 2bath Sleeps 12 nestled on 70 acres
Smart TV

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

Rock Island Hideaway Classic Cozy Apartment in Downtown Owensville Missouri
Owensville
8.4 out of 10, Very Good, (6 reviews)
"Had a good stay would recommend it to anyone"
United States
DWAIN H.
The price is ￥20,011
￥25,134 total
includes taxes & fees
Sep 6 - Sep 7
Rock Island Hideaway Classic Cozy Apartment in Downtown Owensville Missouri
Terrace/patio

4. #1 Cabin at Red Oak Valley

#1 Cabin at Red Oak Valley
Canaan Township
10.0 out of 10, Exceptional, (2 reviews)
"Fabulous"
United States
Moira M.
The price is ￥28,816
￥33,776 total
includes taxes & fees
Sep 1 - Sep 2
#1 Cabin at Red Oak Valley
Exterior

5. Cozy Cabin in the woods near charming Hermann

Cozy Cabin in the woods near charming Hermann
Hermann
9.2 out of 10, Wonderful, (5 reviews)
"The host was very good with the explaining how to get to the property. They also helped us find a place to celebrate our 25th wedding anniversary! Highly recommended location!!!"
United States
Lana
The price is ￥14,696
￥25,800 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cabin in the woods near charming Hermann
Exterior

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

Romantic Glamping Getaway Perfect for Quality Time with Your Partner: Cute Tiny House near Owensville, Missouri
Canaan Township
The price is ￥35,044
￥42,304 total
includes taxes & fees
Sep 1 - Sep 2
Romantic Glamping Getaway Perfect for Quality Time with Your Partner: Cute Tiny House near Owensville, Missouri
Property grounds

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

Primitive Campsites with water spigot, toilets, and wifi!
Bourbon
The price is ￥6,195
￥18,533 total
includes taxes & fees
Sep 1 - Sep 2
Primitive Campsites with water spigot, toilets, and wifi!
Living area

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

Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat
Bourbon
10.0 out of 10, Exceptional, (4 reviews)
"Very charming lil cabin! It was perfect for a solo trip. I’d love to come back with my husband for a romantic weekend getaway."
United States
Wendy L.
The price is ￥19,142
￥57,642 total
includes taxes & fees
Sep 1 - Sep 2
Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat
TV

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

RGM Farms Guesthouse, rural tranquil setting for family & friends to enjoy.
Bourbon
9.8 out of 10, Exceptional, (28 reviews)
"Very cozy and comfortably stay."
United States
Kyle C.
The price is ￥18,586
￥32,554 total
includes taxes & fees
Sep 8 - Sep 9
RGM Farms Guesthouse, rural tranquil setting for family & friends to enjoy.
Property grounds

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

Primitive Campsites with water spigot, toilets, and wifi!
Bourbon
The price is ￥6,195
￥9,890 total
includes taxes & fees
Sep 1 - Sep 2
Primitive Campsites with water spigot, toilets, and wifi!
TV

11. Back Door Guest Suite, Zia My Retreat

Back Door Guest Suite, Zia My Retreat
New Haven
10.0 out of 10, Exceptional, (6 reviews)
"Very comfortable, spacious, great location for canoe trip. "
United States
Carolyn B.
The price is ￥21,612
￥36,854 total
includes taxes & fees
Sep 1 - Sep 2
Back Door Guest Suite, Zia My Retreat
Property grounds

12. 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, (35 reviews)
"Cabin and property are great. Owners keep everything top notch. Bed was not so great."
United States
Joel
The price is ￥12,167
￥24,022 total
includes taxes & fees
Sep 1 - Sep 2
Relax in the Ozark woods at a quiet nature retreat with a private walking trail.
Outdoor dining

13. Rustic Cabin Rental near Meramec State Park, Missouri

Rustic Cabin Rental near Meramec State Park, Missouri
Sullivan
The price is ￥21,132
￥24,334 total
includes taxes & fees
Sep 14 - Sep 15
Rustic Cabin Rental near Meramec State Park, Missouri
Outdoor dining

14. Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (135 reviews)
"Everything was wonderful! It was a great room, a beautiful view from the terrace and a great breakfast."
United States
Kristin V.
The price is ￥15,849
￥25,914 total
includes taxes & fees
Sep 1 - Sep 2
Gipfel Suite - Himmel Haus Bed & Breakfast
Property grounds

15. Get Back to Nature at Three Pine Cabin

Get Back to Nature at Three Pine Cabin
Cuba
9.8 out of 10, Exceptional, (322 reviews)
"The cabin was perfect peaceful andjust perfect."
United States
Bryan B.
The price is ￥18,010
￥31,802 total
includes taxes & fees
Sep 8 - Sep 9
Get Back to Nature at Three Pine Cabin
Property grounds

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

Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
Hermann
10.0 out of 10, Exceptional, (6 reviews)
"This place is AMAZING. It is beautiful and such a peaceful get away. Just a quick 5 minute drive to town, but you feel like you’re miles away. The property was beautiful and the space was peaceful and secluded. Highly recommend. "
United States
Patti
The price is ￥28,016
￥42,832 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
Coffee/tea maker, fridge, microwave, oven

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

Cozy 2-bedroom house in Cuba, MO.
Cuba
9.8 out of 10, Exceptional, (7 reviews)
"Nice spot by Route 66"
United States
Ann W.
The price is ￥15,241
￥21,681 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2-bedroom house in Cuba, MO.
Terrace/patio

18. Fire Pit, 10 private Acres | Pets Welcome

Fire Pit, 10 private Acres | Pets Welcome
Bourbon
10.0 out of 10, Exceptional, (45 reviews)
"Amazing cabin! Our family had a wonderful time. "
United States
Grace S.
The price is ￥28,181
￥69,878 total
includes taxes & fees
Sep 29 - Sep 30
Fire Pit, 10 private Acres | Pets Welcome
TV

19. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.6 out of 10, Exceptional, (15 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥28,016
￥52,539 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom house in fabulous downtown Hermann
Dining

20. Wine Alley East suite

Wine Alley East suite
Hermann
9.4 out of 10, Exceptional, (85 reviews)
"Host was great. Easy checkin and checkout. Great location to ride trolley to wineries and then walk Hermann at night."
United States
Sandy H.
The price is ￥23,213
￥34,651 total
includes taxes & fees
Sep 1 - Sep 2
Wine Alley East suite
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

Pinemark Inn & Suites

Pinemark Inn & Suites

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ Absolutely Loved This Hidden Gem! This hotel was so cute, unique, and charming—it honestly felt like finding a unicorn! We booked the suite, which had two separate rooms and a beautiful tub, and we were so impressed. There were so many adorable little spaces around the property to sit, relax, and enjoy the atmosphere. The pool was absolutely amazing, with beautiful fountains right in the pool. Everything was very clean, beautifully decorated, and smelled fresh and clean. The entire place felt peaceful, relaxing, and refreshing. Honestly, it was nicer than many of the big-name brand hotels we’ve stayed at. It has so much character and charm that you just don’t get at the typical chain hotels. Don’t miss out on this hidden gem! The price is right, the atmosphere is amazing, and it’s definitely a place we would stay again. ❤️"
Ian 1-night trip
Posted 3 hours ago
Pinemark Inn & Suites

Find out more about Rosebud

Search for holiday rentals in Rosebud on Expedia! You can easily find your home rentals, villas, holiday apartments in Rosebud using one of the methods below:

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Look no further and take a look at our great range of rental properties in Rosebud!

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 WiFi 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 Jesse James Wax Museum, 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 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.