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Our top choices for Osage County holiday rentals
Apartment in New Haven
Near Vineyards: Country Condo in New Haven"Clean and loved original architecture."
Richard
The price is 2.731.768 ₫
7.778.184 ₫ total
includes taxes & fees
25 Jan - 26 Jan 2026
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 5.629.826 ₫
6.050.655 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Apartment in New Haven
Studio Stay w/ Deck in Missouri Wine CountryThe price is 2.416.564 ₫
5.892.476 ₫ total
includes taxes & fees
25 Jan - 26 Jan 2026
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 12.686.961 ₫
18.081.152 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
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
Hermann Crown Suites
10/10 Excellent
