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Holiday Rentals in Osage County

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Featured Holiday Rentals in Osage County

Comfy Farm House with a back yard full of fun near Jefferson City, MO. Sleeps 6!

10.0 out of 10, Exceptional, (54)
"Such a cute property for little kids to see! Amazingly clean, and everything you need very peaceful and cozy. And the owners were extremely nice. We will be back."
Comfy Farm House with a back yard full of fun near Jefferson City, MO. Sleeps 6!

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (82)
"Great time wonderful town"
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

Frene Valley Guest House

10.0 out of 10, Exceptional, (77)
"The house is super cute and exactly as listed. It is SO convenient to downtown Hermann shopping and restaurants. Loved having off street parking for our group. Would definitely recommend for a weekend girls trip!"
Frene Valley Guest House

The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

10.0 out of 10, Exceptional, (152)
"It was a great weekend in a cozy cottage "
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

Cozy custom-built cabin - Lakeside

10.0 out of 10, Exceptional, (43)
"This is our second time staying at this property. Love the seclusion and peacefulness of being in the woods but still a short drive to shops and restaurants. "
Cozy custom-built cabin - Lakeside

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

9.8 out of 10, Exceptional, (42)
"We had a wonderful time and were in walking distance of everything we wanted to do. Perfect house for four couples. We had a GREAT time."
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

A Stunning Home, newly constructed & furnished

10.0 out of 10, Exceptional, (55)
"Beautiful home with private baths in every bedroom plus a guest bath. Excellent arrangement for adults coming together for our daughter's Wedding weekend. "
A Stunning Home, newly constructed & furnished

Yurt Floating in the Forest

9.8 out of 10, Exceptional, (26)
"Absolutely love the yurt and the surrounding property! Bill was an excellent host and I made good friends with the Yurt cat that roams the outside of the property. Took a nice stroll around the property while sipping on some excellent coffee. Ran into Bill during my stroll and had a very pleasant conversation! If you’re looking for a peaceful and positive energy space to rest your weary soul, this is the place for you!!"
The price is €160
includes taxes & fees
1 Dec - 2 Dec
Yurt Floating in the Forest

The Farmhouse Inn: 3 bed, 3.5 whole house rental

10.0 out of 10, Exceptional, (93)
"The house was perfect for our girls trip. It was decorated very cute and we loved that we each had our own bathroom. Everything was clean and would definitely recommended to others!"
The price is €406
includes taxes & fees
1 Dec - 2 Dec
The Farmhouse Inn: 3 bed, 3.5 whole house rental

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (154)
"This was our first time staying at a place like this so we had no idea what to expect or what we needed and and didn't need to bring. Everything was awesome! The host had all the bases covered. The setting is beautiful and was perfect for relaxing. We will definitely be back in the future. It was a great experience. "
Cottage Properties - Country Log Cabin

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (42)
"For 2 adults..great amount of space"
The price is €335
includes taxes & fees
5 Dec - 6 Dec
Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Guesthouse - Downtown Historic Hermann

10.0 out of 10, Exceptional, (41)
"We stayed for a weekend during Oktoberfest. We stayed up late playing games, we used the trolley to visit the wineries, and did a little shopping. "
The price is €447
includes taxes & fees
1 Dec - 2 Dec
Ash Creek Guesthouse - Downtown Historic Hermann

Charming 1913 3 Bedroom 2 Bath Dutch Brick Haus

10.0 out of 10, Exceptional, (83)
"This home was everything described and more. The home was cozy and comfortable, beautiful woodwork throughout. Walking distance to downtown Hermann made it so easy to get around. Paul and Heidi were such a joy to meet and visit with. We could not have asked for a better weekend. "
Charming 1913 3 Bedroom 2 Bath Dutch Brick Haus

Great Cabin on Osage River in Tuscumbia, MO

10.0 out of 10, Exceptional, (49)
"Everything we needed was there. Very adorable and charming house. Rhonda was nice on our arrival and showed us through the house. Lots of towels, pans, extra linens, etc My favorite part was seeing the Osage river from the front windows and cute patio. It felt so private and cozy. We will definitely book again. "
Great Cabin on Osage River in Tuscumbia, MO

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (19)
"What an awesome place to visit. "
The price is €283
includes taxes & fees
5 Dec - 6 Dec
Cozy Riverview Cottage. 5 minute walk to downtown

Cozy cabin getaway with hot-tub under stars!

9.4 out of 10, Exceptional, (16)
"toby,the host was a super nice person. Enjoyed talking to him and learning about the area. Very helpful and friendly. "
The price is €222
includes taxes & fees
1 Dec - 2 Dec
Cozy cabin getaway with hot-tub under stars!

Moon-Rise Cabin -Serene and Unique off Katy Trail

10.0 out of 10, Exceptional, (6)
"I have no words to describe how beautiful and mesmerizing the view is from this place. Everything about it is just so lovely. The cabin is hugged by the trees just like in the pictures, and everything is as described and beyond. As a Cleaning business owner, I can attest to how clean and organized it was when we got there. There is everything you need, the host thinks of everything and is on top of things. You only need to bring the ingredients if you are planning on cooking and ice. There are...
The price is €157
includes taxes & fees
8 Dec - 9 Dec
Moon-Rise Cabin -Serene and Unique off Katy Trail

The House on Wine Alley

9.0 out of 10, Wonderful, (36)
"The house was great location to shops & bars. We had a great trip and would recommend the house to anyone "
The price is €311
includes taxes & fees
30 Dec - 31 Dec
The House on Wine Alley

Kork Haus - Whole house rental in Downtown Hermann

9.6 out of 10, Exceptional, (17)
"There was 9 of ladies ages ranging from 35 to 60. The house was an excellent size for our group. Had all the amenities that we needed for a night stay."
The price is €447
includes taxes & fees
11 Dec - 12 Dec
Kork Haus - Whole house rental in Downtown Hermann

Suite on Schiller

9.8 out of 10, Exceptional, (96)
"Great location, very clean, but 1 bed was very hard was only negative. "
Suite on Schiller
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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