Osage County Holiday Rentals

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Our top choices for Osage County holiday rentals

Smart TV, fireplace
Entire Cabin in Linn, MO with all the extras

Entire Cabin in Linn, MO with all the extras

Entire Cabin in Linn, MO with all the extras
Linn
10.0 out of 10, Exceptional, (10 reviews)
"Awesome place!!"
United States
Laura W.
The price is HK$1,559
HK$1,762 total
includes taxes & fees
13 Jan - 14 Jan
Entire Cabin in Linn, MO with all the extras
Exterior
Yurt Floating in the Forest

Yurt Floating in the Forest

Yurt Floating in the Forest
Holts Summit
9.6 out of 10, Exceptional, (43 reviews)
"Its a cool little room to stay in"
United States
Kenneth M.
The price is HK$974
HK$1,286 total
includes taxes & fees
14 Jan - 15 Jan
Yurt Floating in the Forest
Interior
Business or Pleasure - a perfect and cozy get-away!

Business or Pleasure - a perfect and cozy get-away!

Business or Pleasure - a perfect and cozy get-away!
Jefferson City
9.6 out of 10, Exceptional, (29 reviews)
"Perfect place to stay for my trip"
United States
Joshua B.
The price is HK$596
HK$1,268 total
includes taxes & fees
14 Jan - 15 Jan
Business or Pleasure - a perfect and cozy get-away!
Interior
Unique traincar stay at the Katy Caboose!

Unique traincar stay at the Katy Caboose!

Unique traincar stay at the Katy Caboose!
Hartsburg
9.4 out of 10, Exceptional, (10 reviews)
"We loved the 3 taverns in town. Great vibe in a tiny town. "
United States
Dusty
The price is HK$763
HK$1,375 total
includes taxes & fees
13 Jan - 14 Jan
Unique traincar stay at the Katy Caboose!
Interior
Near Vineyards: Country Condo in New Haven

Near Vineyards: Country Condo in New Haven

Near Vineyards: Country Condo in New Haven
3.0 star property
New Haven
"Clean and loved original architecture."
United States
Richard
The price is HK$811
HK$2,308 total
includes taxes & fees
25 Jan - 26 Jan
Near Vineyards: Country Condo in New Haven
Fridge, microwave, oven, stovetop
Get Cozy in the Country - The Cottage on Luca Hill

Get Cozy in the Country - The Cottage on Luca Hill

Get Cozy in the Country - The Cottage on Luca Hill
2.0 star property
Saint James
10.0 out of 10, Exceptional, (18 reviews)
"Nice clean property wirh a good location for us!"
United States
John P.
The price is HK$857
HK$1,458 total
includes taxes & fees
13 Jan - 14 Jan
Get Cozy in the Country - The Cottage on Luca Hill
Living area
The Mercantile on the Katy Trail

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (28 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
The price is HK$1,671
HK$1,796 total
includes taxes & fees
13 Jan - 14 Jan
The Mercantile on the Katy Trail
Fridge, microwave, oven, stovetop
The Carriage House at Parker's Place

The Carriage House at Parker's Place

The Carriage House at Parker's Place
Jefferson City
10.0 out of 10, Exceptional, (46 reviews)
"Perfect location and very comfortable place. "
United States
Holly B.
The price is HK$1,473
HK$2,128 total
includes taxes & fees
15 Jan - 16 Jan
The Carriage House at Parker's Place
TV, video games
Large Unique 2-Bedroom Gamed Themed Loft

Large Unique 2-Bedroom Gamed Themed Loft

Large Unique 2-Bedroom Gamed Themed Loft
Fulton
9.8 out of 10, Exceptional, (43 reviews)
"great overnight stay in the middle of town on our way to Osage Beach from Chicago"
United States
Brady P.
The price is HK$877
HK$1,608 total
includes taxes & fees
13 Jan - 14 Jan
Large Unique 2-Bedroom Gamed Themed Loft
Outdoor dining
Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (114 reviews)
"Nice property, with great view of Hermann"
United States
Mike L.
The price is HK$772
HK$1,307 total
includes taxes & fees
2 Feb - 3 Feb
Gipfel Suite - Himmel Haus Bed & Breakfast
1 bedroom, bed sheets
Cozy cabin getaway with hot-tub under stars!

Cozy cabin getaway with hot-tub under stars!

Cozy cabin getaway with hot-tub under stars!
Ashland
9.6 out of 10, Exceptional, (22 reviews)
"This cabin was great and the setting was amazing. So peaceful! I would definitely stay here again."
United States
Tom M.
The price is HK$1,052
HK$1,847 total
includes taxes & fees
13 Jan - 14 Jan
Cozy cabin getaway with hot-tub under stars!
3 bedrooms, iron/ironing board, WiFi, bed sheets
Archie’s House

Archie’s House

Archie’s House
Berger
10.0 out of 10, Exceptional, (36 reviews)
"Everything was very nice!!! I highly recommend. "
United States
Mary T.
The price is HK$2,322
HK$3,187 total
includes taxes & fees
13 Jan - 14 Jan
Archie’s House
Living area
#3 Cabin at Red Oak Valley

#3 Cabin at Red Oak Valley

#3 Cabin at Red Oak Valley
Canaan Township
10.0 out of 10, Exceptional, (3 reviews)
"Quiet peaceful getaway for my husband and I. All the nature around was incredible! "
United States
Chelsea
The price is HK$1,364
HK$1,642 total
includes taxes & fees
13 Jan - 14 Jan
#3 Cabin at Red Oak Valley
Interior
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace

The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
2.0 star property
Jefferson City
10.0 out of 10, Exceptional, (30 reviews)
"Very clean and well appointed. Nice location."
United States
Thomas C.
The price is HK$1,466
HK$2,262 total
includes taxes & fees
19 Jan - 20 Jan
The Big House, Historic 4-Bedroom Home With Custom Art And Dedicated Workspace
Interior
Downtown Hermann Vacation Home Near Wineries!

Downtown Hermann Vacation Home Near Wineries!

Downtown Hermann Vacation Home Near Wineries!
3.0 star property
Hermann
10.0 out of 10, Exceptional, (1 review)
"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 HK$3,765
HK$5,365 total
includes taxes & fees
13 Jan - 14 Jan
Downtown Hermann Vacation Home Near Wineries!
Outdoor dining
Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
The price is HK$1,403
HK$1,945 total
includes taxes & fees
13 Jan - 14 Jan
Secluded 2 bedroom home close to Hermann
Property grounds
Nature`s Nook by Zia, Hermann

Nature`s Nook by Zia, Hermann

Nature`s Nook by Zia, Hermann
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"This room was so relaxing. Our host was the sweetest. Very attentive. They have gone above and beyond thinking of all the details to make your stay comfortable.We will definitely return again. "
United States
Shelly V.
The price is HK$1,364
HK$2,093 total
includes taxes & fees
12 Feb - 13 Feb
Nature`s Nook by Zia, Hermann
Terrace/patio
Welcome to Rivers Edge Retreat – Your Serene Escape on the Osage River

Welcome to Rivers Edge Retreat – Your Serene Escape on the Osage River

Welcome to Rivers Edge Retreat – Your Serene Escape on the Osage River
Jefferson City
10.0 out of 10, Exceptional, (10 reviews)
"Was fantastic place to stay!"
United States
Veronica W.
The price is HK$982
HK$1,560 total
includes taxes & fees
21 Jan - 22 Jan
Welcome to Rivers Edge Retreat – Your Serene Escape on the Osage River
Interior
The Laughing Boar, perfectly located downtown

The Laughing Boar, perfectly located downtown

The Laughing Boar, perfectly located downtown
Hermann
10.0 out of 10, Exceptional, (55 reviews)
"Great house and location. Would stay here again. "
United States
Valarie H.
The price is HK$3,118
HK$5,480 total
includes taxes & fees
13 Jan - 14 Jan
The Laughing Boar, perfectly located downtown
Living area
A Home Away From Home

A Home Away From Home

A Home Away From Home
2.0 star property
Jefferson City
7.6 out of 10, Good, (4 reviews)
"Very spacious, clean, and easily accessible"
United States
Briana
A Home Away From Home
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

DoubleTree by Hilton Hotel Jefferson City

DoubleTree by Hilton Hotel Jefferson City

10/10 Excellent
"Great all around, would recommend."
Duell 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Jefferson City