A classical building with large columns and detailed carvings.

Cottages in Osage County

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Osage County cottages

1. Yurt Floating in the Forest

Yurt Floating in the Forest
Holts Summit
9.6 out of 10, Exceptional, (60 reviews)
"Nice place to stay."
United States
Patrick O.
The price is AED 459
AED 646 total
includes taxes & fees
20 Oct - 21 Oct
Yurt Floating in the Forest

2. Carriage House at the Mansion on Market Street

Carriage House at the Mansion on Market Street
Hermann
8.0 out of 10, Very good, (18 reviews)
"Great stay, host was very helpful everything you need for a nice weekend in Hermann, MO"
United States
David B.
Carriage House at the Mansion on Market Street

3. The Palmer - A Modern Cottage in Wine Country

The Palmer - A Modern Cottage in Wine Country
Hermann
10.0 out of 10, Exceptional, (5 reviews)
The Palmer - A Modern Cottage in Wine Country

4. Private Guest House-Hermann MO

Private Guest House-Hermann MO
Hermann
10.0 out of 10, Exceptional, (59 reviews)
"We had a great stay!"
United States
Jennifer R.
Private Guest House-Hermann MO

5. Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary
Jefferson City
10.0 out of 10, Exceptional, (62 reviews)
"Amazing place, great communication, easy check in and out! Would absolutely stay again!"
United States
Christina R.
The price is AED 617
AED 966 total
includes taxes & fees
19 Oct - 20 Oct
Historic Carriage House in Jefferson City Near Capitol & Old Penitentiary

6. The Baylor - A cozy wine country cottage

The Baylor - A cozy wine country cottage
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay at the Baylor and loved that we could bring our furry friend as well! The deck was a great spot to relax after a long day of wineries or to enjoy a cup of coffee in the mornings."
United States
Erica H.
The Baylor - A cozy wine country cottage

7. Stumble-In Guest House- Downtown Location

Stumble-In Guest House- Downtown Location
Hermann
10.0 out of 10, Exceptional, (29 reviews)
"Awesome place"
United States
Annetta
Stumble-In Guest House- Downtown Location

8. Jefferson City Bungalow: Hot Tub & Patio!

Jefferson City Bungalow: Hot Tub & Patio!
3.0 star property
Jefferson City
7.6 out of 10, Good, (4 reviews)
"Perfect little get away for my daughter and I. "
United States
Veronica
The price is AED 444
AED 964 total
includes taxes & fees
5 Nov - 6 Nov
Jefferson City Bungalow: Hot Tub & Patio!

9. Updated Berger Cottage w/ Pool, on a Private Farm!

Updated Berger Cottage w/ Pool, on a Private Farm!
Berger
10.0 out of 10, Exceptional, (54 reviews)
"It was great! So fun and such a great space to make memories! "
United States
Lydia L.
Updated Berger Cottage w/ Pool, on a Private Farm!

10. The Rory-A Modern Wine Country Retreat

The Rory-A Modern Wine Country Retreat
Hermann
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for us - we had our dog with us and the combination of the fields/woods around the house and the awesome back deck couldn’t have been better. The cabin was immaculate and well laid out - highly recommended"
United States
Cynthia F.
The Rory-A Modern Wine Country Retreat

11. Serenity House ~ Retreat Near MKT & Vineyards

Serenity House ~ Retreat Near MKT & Vineyards
Hartsburg
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Easy to get to in a quiet location. Management very responsive to messaging. Came stocked with coffee pods, creamer and sugar. Kitchen fully stocked with cooking supplies. "
United States
Ariel E.
Serenity House ~ Retreat Near MKT & Vineyards

12. Hanna's Cottage in the Downtown Historic District of Hermann, Missouri

Hanna's Cottage in the Downtown Historic District of Hermann, Missouri
Hermann
9.6 out of 10, Exceptional, (10 reviews)
"Clean,parking easy to find plenty space. Walking to shops.restaurant near by. If you like the history of town see the museums near by .wine distillery east to find all have reasonable rates for tasting. Enjoyed the porch and yard at the house but will not miss the stairs to the upstairs room, not suited for elderly people otherwise I would stay there again.location perfect very quiet."
United States
Brigitte
Hanna's Cottage in the Downtown Historic District of Hermann, Missouri

13. Scenic Indian House Bluff Cottage is Secluded Above the Gasconade River Valley

Scenic Indian House Bluff Cottage is Secluded Above the Gasconade River Valley
Dixon
10.0 out of 10, Exceptional, (22 reviews)
"The cabin was clean and stocked with plenty of games, blankets, and anything you could need. The beds were very comfortable. The view is stunning. We will be coming back in the fall, just for the view."
United States
Christie
Scenic Indian House Bluff Cottage is Secluded Above the Gasconade River Valley

14. Whole House Rental - Private Cottage near Historic Hermann, Missouri

Whole House Rental - Private Cottage near Historic Hermann, Missouri
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house tucked away from neighbors."
United States
Brandon R.
Whole House Rental - Private Cottage near Historic Hermann, Missouri

15. Secluded Turkey Ridge Cottage Above The River

Secluded Turkey Ridge Cottage Above The River
Dixon
9.8 out of 10, Exceptional, (78 reviews)
"Amazing stay. Great weekend get away."
United States
Ian W.
Secluded Turkey Ridge Cottage Above The River

16. Quaint cottage w/direct access to Katy Trial!

Quaint cottage w/direct access to Katy Trial!
Hartsburg
8.8 out of 10, Excellent, (3 reviews)
" Very convenient to the Katy Trail. Also only a short walk to local venues."
United States
Steve C.
Quaint cottage w/direct access to Katy Trial!

17. Unique traincar stay at the Katy Caboose!

Unique traincar stay at the Katy Caboose!
Hartsburg
9.2 out of 10, Wonderful, (11 reviews)
"Cute fun place to stay for the night! "
United States
Julie S.
Unique traincar stay at the Katy Caboose!

18. Peaceful Guest Home w/ Patio on 152-acre Farm

Peaceful Guest Home w/ Patio on 152-acre Farm
3.0 star property
Berger
10.0 out of 10, Exceptional, (2 reviews)
"Very clean,family friendly, even though it was 7 miles out of town they were very Accommodating,they came to puck us up at the train station and there's a van that will take you into town and you can take the trolley to all the wineries,shopping, we all loved our stay,i would definitely recommend to anyone who enjoys the fram life, they have lots of history, and animals, thank you Susan and Mike for all that you did to make our stay memorable, we would definitely come back. "
United States
Kelly
Peaceful Guest Home w/ Patio on 152-acre Farm

19. Charming Jefferson City Home: 2 Mi to Downtown!

Charming Jefferson City Home: 2 Mi to Downtown!
3.0 star property
Jefferson City
10.0 out of 10, Exceptional, (1 review)
"Nice place "
United States
Consuelo
Charming Jefferson City Home: 2 Mi to Downtown!

20. 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
Downtown Hermann Vacation Home Near Wineries!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Osage County Hotel Reviews

Explore a world of travel with Expedia