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Osage County Holiday Rentals

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Top Holiday Rentals Destinations in Osage County

Our top choices for Osage County holiday rentals

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

10.0 out of 10, Exceptional, (218)
"Beautiful house and property. Fantastic view from deck. Enjoyed heated pool, hot tub, tv/gas fireplace in pool area, kayaking on lake, evening fire pit and star gazing. Owner very responsive and easy to contact. "
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

Entire Cabin in Linn, MO with all the extras

10.0 out of 10, Exceptional, (6)
The price is AU$351
includes taxes & fees
4 Sept - 5 Sept
Entire Cabin in Linn, MO with all the extras

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

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

10.0 out of 10, Exceptional, (22)
"Excellent communication with the property manager and space was exactly as described. Would stay again."
The price is AU$449
includes taxes & fees
15 Sept - 16 Sept
Country Townhouse near Osage River: Go boating, UTV gravel roading, fishing!

The Mercantile on the Katy Trail

4.5 star property
10.0 out of 10, Exceptional, (19)
"Nice quiet area with open concept space inside."
The price is AU$324
includes taxes & fees
9 Sept - 10 Sept
The Mercantile on the Katy Trail

The Pollock Suite is one of our four rooms.

9.8 out of 10, Exceptional, (60)
"Very nice setup and comfortable room. The owners have been incredibly helpful and accomodating."
The price is AU$295
includes taxes & fees
9 Sept - 10 Sept
The Pollock Suite is one of our four rooms.

Glamping with gorgeous sunset views, trolley to all wineries

10.0 out of 10, Exceptional, (3)
"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 AU$353
includes taxes & fees
4 Sept - 5 Sept
Glamping with gorgeous sunset views, trolley to all wineries

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (166)
"Had a great time! "
Cottage Properties - Country Log Cabin

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!!

Unique traincar stay at the Katy Caboose!

10.0 out of 10, Exceptional, (4)
"It was great. A nice stop on the trail. I would recommend this place for anyone who is coming through on the trail. "
The price is AU$274
includes taxes & fees
4 Sept - 5 Sept
Unique traincar stay at the Katy Caboose!

Yurt Floating in the Forest

9.6 out of 10, Exceptional, (35)
"I can now check off "staying in a Yurt" on my bucket list."
The price is AU$255
includes taxes & fees
24 Sept - 25 Sept
Yurt Floating in the Forest

The Monet Suite is one of our four rooms.

10.0 out of 10, Exceptional, (46)
"Beautiful room right next to great night life atmosphere!"
The price is AU$294
includes taxes & fees
4 Sept - 5 Sept
The Monet Suite is one of our four rooms.

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (31)
"Was such a cute cottage! We had a wonderful stay and it was just as described! I would definitely stay there again. "
The price is AU$411
includes taxes & fees
15 Sept - 16 Sept
Cozy Riverview Cottage. 5 minute walk to downtown

Private Logcabin All To Yourself With Lake View

9.8 out of 10, Exceptional, (212)
"Very cool rustic cabin with a neat history."
Private Logcabin All To Yourself With Lake View

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (49)
"This little house was so cute and the perfect size for 2 couples. Great location! We will definitely stay here again. "
The price is AU$388
includes taxes & fees
9 Sept - 10 Sept
Ash Creek Suite - In Downtown Historic Hermann

Brick Bungalow

10.0 out of 10, Exceptional, (58)
"Highly recommend!"
Brick Bungalow

Cozy Cabin in the woods near charming Hermann

Cozy Cabin in the woods near charming Hermann

The Van Gogh Suites is one of our four rooms.

9.6 out of 10, Exceptional, (33)
"Right in the middle of all the action. Loved the neighborhood!"
The price is AU$294
includes taxes & fees
4 Sept - 5 Sept
The Van Gogh Suites is one of our four rooms.

Cozy cabin getaway with hot-tub under stars!

9.6 out of 10, Exceptional, (17)
"We loved the remote location and the quiet and peacefulness of our stay"
The price is AU$392
includes taxes & fees
21 Sept - 22 Sept
Cozy cabin getaway with hot-tub under stars!

The Carriage House at Parker's Place

10.0 out of 10, Exceptional, (39)
"Clean, quaint property. We will try to book this one again next time we're in Jeff City."
The price is AU$383
includes taxes & fees
4 Sept - 5 Sept
The Carriage House at Parker's Place
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

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 favourite 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 depend 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 chosen for you start as low as AU$255 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.