Holiday Rentals in Osage County
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Our top choices for Osage County holiday rentals
Cabin in Linn
Entire Cabin in Linn, MO with all the extras10.0 out of 10, Exceptional, (9)
"Awesome place!!"
Laura W.
The price is €197
includes taxes & fees
29 Dec - 30 Dec
Cottage in Hermann
Downtown Hermann Vacation Home Near Wineries!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...
Tara
The price is €585
includes taxes & fees
29 Dec - 30 Dec
Apartment in Jefferson City
Business or Pleasure - a perfect and cozy get-away!9.6 out of 10, Exceptional, (29)
"Perfect place to stay for my trip"
Joshua B.
The price is €142
includes taxes & fees
30 Dec - 31 Dec
Cottage in Holts Summit
Yurt Floating in the Forest9.6 out of 10, Exceptional, (43)
"Peaceful, quiet, comfortable getaway spot "
Julie
The price is €144
includes taxes & fees
1 Jan - 2 Jan 2026
Cottage in Hartsburg
Unique traincar stay at the Katy Caboose!9.4 out of 10, Exceptional, (10)
"We loved the 3 taverns in town. Great vibe in a tiny town. "
Dusty
The price is €154
includes taxes & fees
29 Dec - 30 Dec
Holiday Home in Saint James
Get Cozy in the Country - The Cottage on Luca Hill10.0 out of 10, Exceptional, (18)
"Nice clean property wirh a good location for us!"
John P.
The price is €163
includes taxes & fees
29 Dec - 30 Dec
Cottage in Jefferson City
The Carriage House at Parker's Place10.0 out of 10, Exceptional, (46)
"Perfect location and very comfortable place. "
Holly B.
The price is €239
includes taxes & fees
29 Dec - 30 Dec
Aparthotel in Hermann
The Mercantile on the Katy Trail9.8 out of 10, Exceptional, (28)
"Great place, fully stocked and clean!"
Lauren
The price is €196
includes taxes & fees
30 Dec - 31 Dec
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.
Top Osage County Hotel Reviews
Inn at Hermannhof
10/10 Excellent
Find out more about Osage County
Holiday Homes in Osage County
Search for holiday homes in Osage County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Osage County using one of the methods below:
- View our selection of featured holiday homes in Osage County
- Use the map to find apartments and other holiday rentals in the Osage County neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday homes in Osage County while they last
Look no further and take a look at our great range of rental properties in Osage County!