Montgomery City Holiday Rentals

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Holiday Rentals in Montgomery City

Frene Valley Guest House

10.0 out of 10, Exceptional, (77)
"The house is super cute and exactly as listed. It is SO convenient to downtown Hermann shopping and restaurants. Loved having off street parking for our group. Would definitely recommend for a weekend girls trip!"
Frene Valley Guest House

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (82)
"Great time wonderful town"
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

10.0 out of 10, Exceptional, (152)
"It was a great weekend in a cozy cottage "
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

9.8 out of 10, Exceptional, (42)
"We had a wonderful time and were in walking distance of everything we wanted to do. Perfect house for four couples. We had a GREAT time."
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

Cozy custom-built cabin - Lakeside

10.0 out of 10, Exceptional, (43)
"This is our second time staying at this property. Love the seclusion and peacefulness of being in the woods but still a short drive to shops and restaurants. "
Cozy custom-built cabin - Lakeside

A Stunning Home, newly constructed & furnished

10.0 out of 10, Exceptional, (55)
"Beautiful home with private baths in every bedroom plus a guest bath. Excellent arrangement for adults coming together for our daughter's Wedding weekend. "
A Stunning Home, newly constructed & furnished

The Farmhouse Inn: 3 bed, 3.5 whole house rental

10.0 out of 10, Exceptional, (93)
"The house was perfect for our girls trip. It was decorated very cute and we loved that we each had our own bathroom. Everything was clean and would definitely recommended to others!"
The price is AU$651
includes taxes & fees
1 Dec - 2 Dec
The Farmhouse Inn: 3 bed, 3.5 whole house rental

Ash Creek Guesthouse - Downtown Historic Hermann

10.0 out of 10, Exceptional, (41)
"We stayed for a weekend during Oktoberfest. We stayed up late playing games, we used the trolley to visit the wineries, and did a little shopping. "
The price is AU$716
includes taxes & fees
1 Dec - 2 Dec
Ash Creek Guesthouse - Downtown Historic Hermann

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (154)
"This was our first time staying at a place like this so we had no idea what to expect or what we needed and and didn't need to bring. Everything was awesome! The host had all the bases covered. The setting is beautiful and was perfect for relaxing. We will definitely be back in the future. It was a great experience. "
Cottage Properties - Country Log Cabin

Wine Alley West Suite

9.2 out of 10, Wonderful, (35)
"Very comfortable stay. Wonderful town."
The price is AU$329
includes taxes & fees
1 Dec - 2 Dec
Wine Alley West Suite

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (42)
"For 2 adults..great amount of space"
The price is AU$536
includes taxes & fees
1 Dec - 2 Dec
Ash Creek Suite - In Downtown Historic Hermann

Charming 1913 3 Bedroom 2 Bath Dutch Brick Haus

10.0 out of 10, Exceptional, (83)
"This home was everything described and more. The home was cozy and comfortable, beautiful woodwork throughout. Walking distance to downtown Hermann made it so easy to get around. Paul and Heidi were such a joy to meet and visit with. We could not have asked for a better weekend. "
Charming 1913 3 Bedroom 2 Bath Dutch Brick Haus

The Artists Suites, Leonardo da Vinci Suite

9.8 out of 10, Exceptional, (28)
"The room was very cute located within a lovely building. Good walking distance from all the things. The patio and deck were nice. The street traffic from Market street was a little loud at night. Overall it was a nice trip. "
The Artists Suites, Leonardo da Vinci Suite

Modern Victorian - 1910 Guesthaus

10.0 out of 10, Exceptional, (25)
"The house is very clean and the beds are comfy!"
Modern Victorian - 1910 Guesthaus

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (19)
"What an awesome place to visit. "
The price is AU$454
includes taxes & fees
1 Dec - 2 Dec
Cozy Riverview Cottage. 5 minute walk to downtown

The Bittersweet Inn: Brand new 6 bed 5 bath house

10.0 out of 10, Exceptional, (69)
"We could not have been happier with our stay at The Bittersweet Inn. The house was spotless, spacious, and bright. All furnishings are new and comfortable. The host was prompt with communication, friendly, and helpful. "
The Bittersweet Inn: Brand new 6 bed 5 bath house

The House on Wine Alley

9.0 out of 10, Wonderful, (36)
"The house was great location to shops & bars. We had a great trip and would recommend the house to anyone "
The price is AU$500
includes taxes & fees
1 Dec - 2 Dec
The House on Wine Alley

Kork Haus - Whole house rental in Downtown Hermann

9.6 out of 10, Exceptional, (17)
"There was 9 of ladies ages ranging from 35 to 60. The house was an excellent size for our group. Had all the amenities that we needed for a night stay."
The price is AU$716
includes taxes & fees
1 Dec - 2 Dec
Kork Haus - Whole house rental in Downtown Hermann

Suite on Schiller

9.8 out of 10, Exceptional, (96)
"Great location, very clean, but 1 bed was very hard was only negative. "
Suite on Schiller

Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

10.0 out of 10, Exceptional, (130)
"The location was great. Everything within walking distance. "
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
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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Other types of properties in Montgomery City you may be interested in

Baymont by Wyndham Warrenton

2.5 star property
7.2 out of 10, Good, (879)
"Friendly staff . quick check in , clean , good breakfast (many choices)."
The price is AU$121
includes taxes & fees
1 Dec - 2 Dec
Baymont by Wyndham Warrenton

Baymont by Wyndham Fulton

2.5 star property
8.4 out of 10, Very good, (812)
"It was fair bang for the buck. Clean, quiet, freindly. About what I expected."
The price is AU$133
includes taxes & fees
2 Dec - 3 Dec
Baymont by Wyndham Fulton

Hermann Crown Suites

3.5 star property
9.4 out of 10, Exceptional, (637)
"If you need handicap accessible, do not rely on the description you need to call the property!!"
The price is AU$416
includes taxes & fees
7 Dec - 8 Dec
Hermann Crown Suites
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Montgomery City?

Yes, there are holiday rentals close to the most popular sights in Montgomery City, or you can select a more secluded option if you're looking for a relaxing stay. Montgomery City is known for its parks.

What are some of the best holiday rentals that Montgomery City has to offer?

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! : This holiday home rental outside of Montgomery City offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What’s there to see and do in Montgomery City?

While you're exploring the area, Graham Cave State Park and Katy Trail - McKittrick Trailhead are a couple of picturesque spots to get outside and enjoy nature. Stone Hill Winery and Endless Summer Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Montgomery City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery City. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.