Montgomery City Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Montgomery City vacation rentals

Interior

Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (1 review)
"This place was seriously a slice of heaven. The hosts were very attentive and welcoming! The house was fully stocked with anything we may have needed, we will definitely be back!"
United States
Kylee F.
The price is ￥19,398
￥33,475 total
includes taxes & fees
Mar 30 - Mar 31
Papa's Cabin - 40 acres & 5 acre lake!
Room

Scenic Nature-Side Stay Near I-70 With Fruit Trees

Scenic Nature-Side Stay Near I-70 With Fruit Trees
High Hill
The price is ￥22,796
￥27,706 total
includes taxes & fees
Mar 30 - Mar 31
Scenic Nature-Side Stay Near I-70 With Fruit Trees
Outdoor dining

Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (118 reviews)
"Host was welcoming. Christmas Lights were great. Breakfast was also great."
United States
David N.
The price is ￥15,871
￥25,950 total
includes taxes & fees
Mar 30 - Mar 31
Gipfel Suite - Himmel Haus Bed & Breakfast
Smart TV

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Hermann
9.6 out of 10, Exceptional, (7 reviews)
"The home was very clean and had everything we needed. Very quiet area out in the country. Enjoyed our stay there and would highly recommend staying there."
United States
Sheri D.
The price is ￥32,463
￥58,775 total
includes taxes & fees
Mar 30 - Mar 31
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Property grounds

The Da Vinci Suite is one of our four rooms.

The Da Vinci Suite is one of our four rooms.
Hermann
9.8 out of 10, Exceptional, (55 reviews)
"Great location, cool place"
United States
Dave J.
The price is ￥19,045
￥32,957 total
includes taxes & fees
Mar 30 - Mar 31
The Da Vinci Suite is one of our four rooms.
Fridge, microwave, oven, stovetop

Glamping with gorgeous sunset views, trolley to all wineries

Glamping with gorgeous sunset views, trolley to all wineries
Berger
9.6 out of 10, Exceptional, (9 reviews)
"Nice place to stay, super clean and cute! "
United States
Amanda E.
The price is ￥24,047
￥33,573 total
includes taxes & fees
Apr 6 - Apr 7
Glamping with gorgeous sunset views, trolley to all wineries
Comfort Loft, 2 Queen Beds, Bathtub, Garden View | Living area | 45-inch Smart TV with digital channels, books, streaming services

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (29 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
The price is ￥35,091
￥37,714 total
includes taxes & fees
Apr 6 - Apr 7
The Mercantile on the Katy Trail
House (3 Bedrooms) | Interior

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 ￥77,430
￥110,351 total
includes taxes & fees
Mar 30 - Mar 31
Downtown Hermann Vacation Home Near Wineries!
TV

Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
10.0 out of 10, Exceptional, (6 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥20,039
￥42,593 total
includes taxes & fees
Mar 30 - Mar 31
Charming 2-bedroom house in fabulous downtown Hermann
Interior

Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (47 reviews)
"The VRBO was clean and very warming! We had a great time! "
United States
Amy R.
The price is ￥23,245
￥34,859 total
includes taxes & fees
Mar 30 - Mar 31
Wine Alley West Suite
Outdoor dining

Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann
Hermann
9.4 out of 10, Exceptional, (52 reviews)
"Such a great place to stay! "
United States
Anonymous traveler
The price is ￥20,039
￥40,432 total
includes taxes & fees
Mar 30 - Mar 31
Ash Creek Suite - In Downtown Historic Hermann
Outdoor dining

The Pollock Suite is one of our four rooms.

The Pollock Suite is one of our four rooms.
Hermann
9.8 out of 10, Exceptional, (68 reviews)
"Welcoming host and very cozy place, Christmas decorations were great!"
United States
Dylan S.
The price is ￥19,045
￥32,957 total
includes taxes & fees
Mar 30 - Mar 31
The Pollock Suite is one of our four rooms.
Fridge, microwave, oven, stovetop

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Hermann
The price is ￥36,358
￥45,611 total
includes taxes & fees
Mar 31 - Apr 1
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Outdoor dining

The Van Gogh Suites is one of our four rooms.

The Van Gogh Suites is one of our four rooms.
Hermann
9.6 out of 10, Exceptional, (42 reviews)
"Great location, clean"
United States
Chris J.
The price is ￥19,045
￥32,957 total
includes taxes & fees
Mar 30 - Mar 31
The Van Gogh Suites is one of our four rooms.
Interior

Studio 1892 Guesthouse Step out front door into Historic Downtown Hermann!

Studio 1892 Guesthouse Step out front door into Historic Downtown Hermann!
Hermann
The price is ￥58,914
￥80,235 total
includes taxes & fees
Apr 12 - Apr 13
Studio 1892 Guesthouse Step out front door into Historic Downtown Hermann!
Dining

Wine Alley East suite

Wine Alley East suite
Hermann
9.4 out of 10, Exceptional, (77 reviews)
"Great location "
United States
Scotti
The price is ￥23,245
￥34,859 total
includes taxes & fees
Apr 1 - Apr 2
Wine Alley East suite
Exterior detail

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
McKittrick
10.0 out of 10, Exceptional, (2 reviews)
"Loved this placed, would definitely come back!"
United States
Cody W.
The price is ￥36,358
￥45,611 total
includes taxes & fees
Mar 31 - Apr 1
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
Property grounds

Nature`s Nook by Zia, Hermann

Nature`s Nook by Zia, Hermann
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"This place is AMAZING. It is beautiful and such a peaceful get away. Just a quick 5 minute drive to town, but you feel like you’re miles away. The property was beautiful and the space was peaceful and secluded. Highly recommend. "
United States
Patti
The price is ￥28,054
￥43,051 total
includes taxes & fees
Apr 6 - Apr 7
Nature`s Nook by Zia, Hermann
Outdoor dining

Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (46 reviews)
"House was very clean and welcoming. Beds were comfortable. Property was beautiful "
United States
Adam F.
The price is ￥28,856
￥40,671 total
includes taxes & fees
Mar 30 - Mar 31
Secluded 2 bedroom home close to Hermann
Outdoor dining

The Monet Suite is one of our four rooms.

The Monet Suite is one of our four rooms.
Hermann
10.0 out of 10, Exceptional, (56 reviews)
"Great location, comfortable room, quiet at night. Live music and patios nearby."
United States
Laura L.
The price is ￥19,045
￥32,957 total
includes taxes & fees
Apr 2 - Apr 3
The Monet Suite is one of our four rooms.
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 City Hotel Reviews

Inn at Hermannhof

Inn at Hermannhof

10/10 Excellent
"Cozy, clean room with great views of Hermann. "
Kari 1-night trip
Posted 1 day ago
Inn at Hermannhof

Find out more about Montgomery City

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Look no further and take a look at our great range of rental properties in Montgomery City!

Frequently asked questions

Can I find a vacation rental in Montgomery City?

Yes, we have vacation rentals close to top sights in Montgomery City, or you can go with a secluded option if you'd like a relaxing place to stay. Montgomery City is known for its parks.

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

Farmhouse on 6th St: This vacation home rental outside of Montgomery City is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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

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

What’s a vacation rental in Montgomery City like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Montgomery City. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for families.