Top Cottages in Montgomery County in 2026

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Top Cities in Montgomery County

A mountain bike parked on a dirt path surrounded by trees.

Our top choices for Montgomery County cottages

A two-story house with a dark facade, a central entrance, and a picket fence in the front yard.

1. Private Guest House-Hermann MO

Hermann

Maria D.

A covered outdoor area with a wooden deck, seating, a TV mounted on the wall, and a view of a green landscape.

2. The Palmer - A Modern Cottage in Wine Country

Hermann

Rachel D.

A covered outdoor area with a table and chairs, a ceiling fan, and a view of a green landscape.

3. The Baylor - A cozy wine country cottage

Hermann

Jenny D.

A single-story house with a front porch, a small front yard, and a tree.

4. Stumble-In Guest House- Downtown Location

Hermann

Madalyn G.

A wooden house with a metal roof, a porch, and a fenced area.

5. The Paddock House at Dark Horse Farms. 3Bd 2bath Sleeps 12 nestled on 70 acres

Owensville

Shane B.

HK$2,429 total

includes taxes & fees

15 Sept - 16 Sept

A wooden deck with two chairs and a white railing, overlooking a green landscape with a fence and trees.

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

Berger

Lydia L.

A red single-story house with a grey roof, a front porch, and a gravel driveway.

7. The Rory-A Modern Wine Country Retreat

Hermann

A wooden deck with a dining table and chairs, surrounded by glass walls and a red umbrella.

8. Tarnhouse Chalet | Dock + Fireplace

Innsbrook

Elisha K.

A two-story house with a sloped roof, a covered porch, and a staircase leading to the upper level.

9. Private Lakeside A-Frame | Hot Tub & 3 Acres

Innsbrook

Laura W.

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

Hermann

Marcus J.

A small, wooden structure with a porch and a lattice door, surrounded by a stone wall and a white picket fence.

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

Hermann

Brandon R.

An outdoor covered patio with a grill and seating area, overlooking a grassy field.

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

Berger

"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. "

Kelly

A patio with a fire pit, outdoor furniture, and a wooden deck.

13. Downtown Hermann Vacation Home Near Wineries!

Hermann

"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

A two-story house with a front porch, a welcome sign, and a star decoration.

14. Half-mi to Boat Ramp! Gasconade Country Cottage

Morrison

A wooden deck with outdoor furniture, a grill, and a large air conditioning unit.

15. Home w/ Trail Access on 19 Acres in Wright City!

Wright City

Mike

A glass-top table with chairs and a bowl of fruit on a wooden deck surrounded by trees.

16. Hot Tub & Barrel Sauna: Lakefront Innsbrook Chalet

Wright City

A wooden cabin with a sloped roof, a wooden deck leading to the entrance, and a window with a wreath.

17. Quiet Lakefront Cottage With Dock & Resort Access!

Wright City

JESSICA

A cozy cabin interior with a wooden ceiling, a large window with blinds, a sofa, a small table with a lamp, and a staircase.

18. Close to Vineyards: Updated New Haven Retreat!

New Haven

Kizzy

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

Berger

Sarah

A rustic wooden building labeled "WM WINERY" with a gravel driveway and large rocks in front.

20. Spacious Owensville Getaway w/ Winery On-site!

Rosebud

"I don't even know where to start with this rental. We live in the country, this farmhouse was right up our alley!! I have stayed in a lot of rental properties, this one was like being at home. I could have stayed forever. The pond served as a wonderful experience for my daughter, she loves to fish and caught many fish. My husband enjoyed watching the sunrise every morning with his cup of coffee. The restaurant was in a league of it's own, the food was spectacular. The owner was VERY responsive,...

Elizabeth

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Top Montgomery County Hotel Reviews

Captain Wohlt Inn Bed & Breakfast

10/10 Excellent

"The property was very clean. check in was simple. at check in they were very specific on what remotes worked and also set up key codes on the spot. Room was very clean and fit our needs perfectly."