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Cottages in Montgomery County

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Top Cities in Montgomery County

Our top choices for Montgomery County cottages

1. Private Guest House-Hermann MO

Private Guest House-Hermann MO
Hermann
10.0 out of 10, Exceptional, (52 reviews)
"Perfect for the weekend, the host was super communicative and the house was clean and well maintained. Definitely recommend for a quaint stay in Hermann."
United States
Maria D.
Private Guest House-Hermann MO

2. The Palmer - A Modern Cottage in Wine Country

The Palmer - A Modern Cottage in Wine Country
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"Great home! We would definitely rent here again. The views, privacy and cabin are top notch! Close to town too. We highly recommend this place for others."
United States
Rachel D.
The Palmer - A Modern Cottage in Wine Country

3. The Baylor - A cozy wine country cottage

The Baylor - A cozy wine country cottage
Hermann
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was pristine and beautiful and the deck space was amazing with beautiful views. The only downside to this cozy cottage was the road noise."
United States
Jenny D.
The Baylor - A cozy wine country cottage

4. Stumble-In Guest House- Downtown Location

Stumble-In Guest House- Downtown Location
Hermann
10.0 out of 10, Exceptional, (23 reviews)
"Perfect location to enjoy and walk all around downtown Hermann!"
United States
Madalyn G.
Stumble-In Guest House- Downtown Location

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

The Paddock House at Dark Horse Farms. 3Bd 2bath Sleeps 12 nestled on 70 acres
Owensville
10.0 out of 10, Exceptional, (2 reviews)
"Wished we could stay longer!"
United States
Shane B.
The price is HK$1,341
HK$2,429 total
includes taxes & fees
15 Sept - 16 Sept
The Paddock House at Dark Horse Farms. 3Bd 2bath Sleeps 12 nestled on 70 acres

6. 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!

7. The Rory-A Modern Wine Country Retreat

The Rory-A Modern Wine Country Retreat
Hermann
The Rory-A Modern Wine Country Retreat

8. Tarnhouse Chalet | Dock + Fireplace

Tarnhouse Chalet | Dock + Fireplace
Innsbrook
9.4 out of 10, Exceptional, (3 reviews)
"Great home, great location! Priced high for the area and size of the home."
United States
Elisha K.
Tarnhouse Chalet | Dock + Fireplace

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

Private Lakeside A-Frame | Hot Tub & 3 Acres
Innsbrook
8.0 out of 10, Very good, (3 reviews)
"Loved the private property, access to Innsbruck, and time in the hot tub. Hope to return!"
United States
Laura W.
Private Lakeside A-Frame | Hot Tub & 3 Acres

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

Hanna's Cottage in the Downtown Historic District of Hermann, Missouri
Hermann
9.8 out of 10, Exceptional, (9 reviews)
"It was perfect and in a great area."
United States
Marcus J.
Hanna's Cottage in the Downtown Historic District of Hermann, Missouri

11. 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

12. 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

13. 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!

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

Half-mi to Boat Ramp! Gasconade Country Cottage
3.0 star property
Morrison
Half-mi to Boat Ramp! Gasconade Country Cottage

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

Home w/ Trail Access on 19 Acres in Wright City!
3.0 star property
Wright City
10.0 out of 10, Exceptional, (1 review)
"Great house in a beautiful setting. We enjoyed the quiet solitude and woodsy area. Very clean accommodations with every amenity available. "
United States
Mike
Home w/ Trail Access on 19 Acres in Wright City!

16. Hot Tub & Barrel Sauna: Lakefront Innsbrook Chalet

Hot Tub & Barrel Sauna: Lakefront Innsbrook Chalet
3.0 star property
Wright City
Hot Tub & Barrel Sauna: Lakefront Innsbrook Chalet

17. Quiet Lakefront Cottage With Dock & Resort Access!

Quiet Lakefront Cottage With Dock & Resort Access!
3.0 star property
Wright City
10.0 out of 10, Exceptional, (1 review)
"This property was gorgeous and a perfect place for anyone who likes nature and it’s beauty. The owners are very kind and always available. Highly recommended. We will be back! Thank you for sharing your piece of paradise with my family. "
United States
JESSICA
Quiet Lakefront Cottage With Dock & Resort Access!

18. Close to Vineyards: Updated New Haven Retreat!

Close to Vineyards: Updated New Haven Retreat!
3.0 star property
New Haven
10.0 out of 10, Exceptional, (1 review)
"Very clean and relaxing environment!! "
United States
Kizzy
Close to Vineyards: Updated New Haven Retreat!

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

Updated Berger Cottage w/ Pool, on a Private Farm!
3.0 star property
Berger
10.0 out of 10, Exceptional, (1 review)
"Only positive things to say about our trip. Would 100% recommend to anyone wanting a quiet get away with family and friends. Far enough away from town to kick back and relax but close enough to the shops, restaurants, and wineries to enjoy all that Hermann has to offer!"
United States
Sarah
Updated Berger Cottage w/ Pool, on a Private Farm!

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

Spacious Owensville Getaway w/ Winery On-site!
2.0 star property
Rosebud
10.0 out of 10, Exceptional, (1 review)
"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,...
United States
Elizabeth
Spacious Owensville Getaway w/ Winery On-site!
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 Montgomery County Hotel Reviews

Find out more about Montgomery County

Montgomery County Cottages information

Number of reviews
162
Accommodation
35 Cottages
Lowest Price
HK$2,429
Highest Price
HK$2,429

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