Osage County Holiday Rentals

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Our top choices for Osage County holiday rentals

10.0 out of 10, Exceptional, (9)
"Awesome place!!"
United States
Laura W.
The price is NZ$387
includes taxes & fees
29 Dec - 30 Dec
Entire Cabin in Linn, MO with all the extras
3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a very cute little house on the end of a quiet street. It's within easy walking distance of all the shops, restaurants, wineries, distilleries, and bars between 1st Street and 5th Street. If you don't mind a longer, hillier walk you could also go further south to City Park or to Stone Hill winery. But there's also easy transportation on the Trolley or local ride services. We were happy to find there were more beds than pictured (3 queen size downstairs between 2 bedrooms, and 2 queens...
United States
Tara
The price is NZ$1,180
includes taxes & fees
29 Dec - 30 Dec
Downtown Hermann Vacation Home Near Wineries!
9.6 out of 10, Exceptional, (29)
"Perfect place to stay for my trip"
United States
Joshua B.
The price is NZ$279
includes taxes & fees
30 Dec - 31 Dec
Business or Pleasure - a perfect and cozy get-away!

Cottage in Holts Summit

Yurt Floating in the Forest
9.6 out of 10, Exceptional, (43)
"Peaceful, quiet, comfortable getaway spot "
United States
Julie
The price is NZ$283
includes taxes & fees
1 Jan - 2 Jan 2026
Yurt Floating in the Forest
9.4 out of 10, Exceptional, (10)
"We loved the 3 taverns in town. Great vibe in a tiny town. "
United States
Dusty
The price is NZ$302
includes taxes & fees
29 Dec - 30 Dec
Unique traincar stay at the Katy Caboose!
2.0 star property
10.0 out of 10, Exceptional, (18)
"Nice clean property wirh a good location for us!"
United States
John P.
The price is NZ$321
includes taxes & fees
29 Dec - 30 Dec
Get Cozy in the Country - The Cottage on Luca Hill

Cottage in Jefferson City

The Carriage House at Parker's Place
10.0 out of 10, Exceptional, (46)
"Perfect location and very comfortable place. "
United States
Holly B.
The price is NZ$468
includes taxes & fees
29 Dec - 30 Dec
The Carriage House at Parker's Place
4.5 star property
9.8 out of 10, Exceptional, (28)
"Great place, fully stocked and clean!"
United States
Lauren
The price is NZ$395
includes taxes & fees
30 Dec - 31 Dec
The Mercantile on the Katy Trail
10.0 out of 10, Exceptional, (30)
"Very clean and well appointed. Nice location."
United States
Thomas C.
The price is NZ$509
includes taxes & fees
5 Jan - 6 Jan 2026
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
10.0 out of 10, Exceptional, (10)
"Was fantastic place to stay!"
United States
Veronica W.
The price is NZ$341
includes taxes & fees
5 Jan - 6 Jan 2026
Welcome to Rivers Edge Retreat – Your Serene Escape on the Osage River
9.6 out of 10, Exceptional, (22)
"This cabin was great and the setting was amazing. So peaceful! I would definitely stay here again."
United States
Tom M.
The price is NZ$406
includes taxes & fees
29 Dec - 30 Dec
Cozy cabin getaway with hot-tub under stars!
3.0 star property
"Clean and loved original architecture."
United States
Richard
The price is NZ$507
includes taxes & fees
25 Jan - 26 Jan 2026
Near Vineyards: Country Condo in New Haven
10.0 out of 10, Exceptional, (3)
"Beautiful house tucked away from neighbors."
United States
Brandon R.
Whole House Rental - Private Cottage near Historic Hermann, Missouri
9.8 out of 10, Exceptional, (43)
"great overnight stay in the middle of town on our way to Osage Beach from Chicago"
United States
Brady P.
The price is NZ$353
includes taxes & fees
1 Jan - 2 Jan 2026
Large Unique 2-Bedroom Gamed Themed Loft
The price is NZ$334
includes taxes & fees
29 Dec - 30 Dec
Rock Island Hideaway Classic Cozy Apartment in Downtown Owensville Missouri
The price is NZ$452
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 2-bedroom apartment in wonderful Jefferson City with WiFi, AC
9.2 out of 10, Wonderful, (9)
"Wonderful cabin. Absolutely recommend!!"
United States
Vivian
Charming cabin with WiFi and AC in delightful Eldon
10.0 out of 10, Exceptional, (54)
"Great house and location. Would stay here again. "
United States
Valarie H.
The price is NZ$1,206
includes taxes & fees
29 Dec - 30 Dec
The Laughing Boar, perfectly located downtown
9.8 out of 10, Exceptional, (68)
"Great location, plenty of amenities, gracious host, shops and restaurants immediately nearby"
United States
Brandon R.
The price is NZ$352
includes taxes & fees
29 Dec - 30 Dec
The Pollock Suite is one of our four rooms.

Holiday Home in New Florence

Secluded 2 bedroom home close to Hermann
9.8 out of 10, Exceptional, (46)
"We thoroughly enjoyed our stay! The house was very clean and spacious for our group of 6. Very happy with our experience!"
United States
Renee R.
The price is NZ$428
includes taxes & fees
29 Dec - 30 Dec
Secluded 2 bedroom home close to Hermann
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

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$283 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.