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Osage County Holiday Rentals

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Top Holiday Rentals Destinations in Osage County

Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace
A heated pool

Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

10.0 out of 10, Exceptional, (219)
"Such a great place to connect with family or friends. "
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace
Entire Cabin in Linn, MO with all the extras
Microwave, oven, stovetop, dishwasher

Entire Cabin in Linn, MO with all the extras

10.0 out of 10, Exceptional, (8)
"We had a lovely stay. The cabin was in pristine shape and had everything we needed to enjoy our stay. Roxie was accommodating and responsive. We would definitely stay again. "
The price is NZ$392
includes taxes & fees
29 Sept - 30 Sept
Entire Cabin in Linn, MO with all the extras
Country Townhouse near Osage River: Go boating, UTV gravel roading, fishing!
Exterior detail

Country Townhouse near Osage River: Go boating, UTV gravel roading, fishing!

10.0 out of 10, Exceptional, (23)
"Excellent communication with the property manager and space was exactly as described. Would stay again."
Country Townhouse near Osage River: Go boating, UTV gravel roading, fishing!
Cozy house nestled in the country
Exterior

Cozy house nestled in the country

10.0 out of 10, Exceptional, (17)
"Very cozy, plenty of space, well maintained. We had a great time!"
Cozy house nestled in the country
The Mercantile on the Katy Trail
Front of property

The Mercantile on the Katy Trail

4.5 star property
9.8 out of 10, Exceptional, (22)
"Nice quiet area with open concept space inside."
The price is NZ$376
includes taxes & fees
30 Sept - 1 Oct
The Mercantile on the Katy Trail
Suite on Schiller
Fridge, microwave, oven, coffee/tea maker

Suite on Schiller

9.8 out of 10, Exceptional, (110)
"Great place to stay and location was perfect."
Suite on Schiller
Cozy Cabin in the woods near charming Hermann
Exterior

Cozy Cabin in the woods near charming Hermann

Cozy Cabin in the woods near charming Hermann
Country Container Tiny House. Experience peace by the water & native wildlife!
Property grounds

Country Container Tiny House. Experience peace by the water & native wildlife!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Was the perfect place to stay while visiting our daughter at WestMo. If you’re looking for a tiny house experience, this is the one for you.. "
The price is NZ$225
includes taxes & fees
5 Oct - 6 Oct
Country Container Tiny House. Experience peace by the water & native wildlife!
Private Logcabin All To Yourself With Lake View
Property grounds

Private Logcabin All To Yourself With Lake View

9.8 out of 10, Exceptional, (213)
"Very cool rustic cabin with a neat history."
Private Logcabin All To Yourself With Lake View
Ash Creek Suite - In Downtown Historic Hermann
Dining

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (49)
"Great location in a lovely town."
The price is NZ$432
includes taxes & fees
29 Sept - 30 Sept
Ash Creek Suite - In Downtown Historic Hermann
Glamping with gorgeous sunset views, trolley to all wineries
Fridge, microwave, oven, stovetop

Glamping with gorgeous sunset views, trolley to all wineries

9.4 out of 10, Exceptional, (6)
"It was a wonderful stay for 5 of us girls going to Herman for a day at the Winery. This location was perfect, just 7 minutes up the road from Downtown Herman. The trolley picked us up with no issue. Very quiet location, perfect for a quick getaway!"
The price is NZ$395
includes taxes & fees
29 Sept - 30 Sept
Glamping with gorgeous sunset views, trolley to all wineries
Cottage Properties - Country Log Cabin
TV, fireplace, DVD player, stereo

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (167)
"Had a great time! "
Cottage Properties - Country Log Cabin
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Interior

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

9.6 out of 10, Exceptional, (99)
"Great stay . Perfect for 3 couples. House was exactly as described with a great location. Would 100% stay here again! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
Interior

Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

10.0 out of 10, Exceptional, (146)
"We stay here each year for a bike race weekend. We really enjoy the space and the location!!"
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
Cozy Riverview Cottage. 5 minute walk to downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (33)
"We had a great stay at Autzie’s and was the perfect setting for our 20th wedding anniversary getaway. Thanks"
The price is NZ$461
includes taxes & fees
30 Sept - 1 Oct
Cozy Riverview Cottage. 5 minute walk to downtown
The Van Gogh Suites is one of our four rooms.
Outdoor dining

The Van Gogh Suites is one of our four rooms.

9.6 out of 10, Exceptional, (35)
"This was our second time to say at the Artist Suites. We enjoy staying here because each suite is unique and we like the downtown location. Next time we visit Hermann we will once again stay here "
The price is NZ$330
includes taxes & fees
30 Sept - 1 Oct
The Van Gogh Suites is one of our four rooms.
The Pollock Suite is one of our four rooms.
Property grounds

The Pollock Suite is one of our four rooms.

9.8 out of 10, Exceptional, (62)
"We had a really nice stay and would definitely book again."
The price is NZ$330
includes taxes & fees
30 Sept - 1 Oct
The Pollock Suite is one of our four rooms.
The Carriage House at Parker's Place
Fridge, microwave, oven, stovetop

The Carriage House at Parker's Place

10.0 out of 10, Exceptional, (40)
"Carefully re-habbed. Tastefully decorated. "
The price is NZ$515
includes taxes & fees
5 Oct - 6 Oct
The Carriage House at Parker's Place
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Dining

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

9.8 out of 10, Exceptional, (63)
"It is verry pretty inside, loved the decorations, it had 2 king beds, a great out door area. We loved it because of the location. Its two houses down from the Tin Mill."
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
New - custom-built Treehouse - Twilight
Interior

New - custom-built Treehouse - Twilight

10.0 out of 10, Exceptional, (3)
"The twilight cabin was so clean and cozy. We enjoyed our stay. "
New - custom-built Treehouse - Twilight
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 Osage County Hotel Reviews

Days Inn by Wyndham Jefferson City

Days Inn by Wyndham Jefferson City

10/10 Excellent
"We stay here every time we are in Jefferson City because it's always clean and comfortable. "
Cary 1-night trip
Posted 6 days ago
Days Inn by Wyndham Jefferson City

Find out more about Osage County

Find out more about Osage County

Everything you need to know about Osage County holiday rentals

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

Osage County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osage County. 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 Osage County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osage County holiday rentals we have selected for you start as low as NZ$225 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osage County rentals

At Expedia, we put the best Osage County holiday 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 Osage County 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 Osage County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osage County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.