Montgomery City Vacation Rentals

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Vacation Rentals in Montgomery City

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Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
10.0 out of 10, Exceptional, (12)
"Awakened at 2:30 AM Saturday night to a commotion across the street. Several adults in a shouting match for over a half hour. Police arrived."
The price is CA $410
CA $679 total
includes taxes & fees
May 15 - May 16
Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
Interior
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
9.6 out of 10, Exceptional, (64)
"This place was so cute! My group of 7 stayed and it was absolutely perfect! The size was great, the history was fun, and everything worked perfectly. The kitchen and bathrooms have been updated so no worries about anything being outdated/nonfunctional. The trolly picks you up right at the street. Its all amazing! And the hosts were a joy to work with!"
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Fridge, microwave, coffee/tea maker, toaster
Ash Creek Suite - In Downtown Historic Hermann
9.4 out of 10, Exceptional, (36)
"It was very nice and had a lot to do in walking distance."
The price is CA $273
CA $469 total
includes taxes & fees
May 15 - May 16
Ash Creek Suite - In Downtown Historic Hermann
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Fridge, microwave, oven, coffee/tea maker
Suite on Schiller
9.8 out of 10, Exceptional, (83)
"We so enjoyed our stay. The prop"
Suite on Schiller
Free WiFi, bed sheets
Cottage Properties - Country Log Cabin
10.0 out of 10, Exceptional, (141)
"We had a great time. The cabin was at a good location just off of the highway. If you want to go to Herman, you may want to use the paved road. Hanging out with the horses and outside was nice. We went to Herman and Jonesburg for a day trip and hung out at the cabin playing games till late."
Cottage Properties - Country Log Cabin
Fridge, microwave, oven, stovetop
New home in Historic downtown Hermann
10.0 out of 10, Exceptional, (24)
"The house was so inviting and beautifully updated! It was a short walk away from all of the bars and shops downtown and the Trolley picked you up right outside which was fantastic!! We had such a fun birthday weekend and the house and amenities made the stay that much better!"
The price is CA $410
CA $789 total
includes taxes & fees
May 15 - May 16
New home in Historic downtown Hermann
Interior
Suite #2 - 1 Bed 1 Bath in Downtown Hermann
10.0 out of 10, Exceptional, (55)
"The location was great, and the property was clean and easy! Loved it!"
Suite #2 - 1 Bed 1 Bath in Downtown Hermann
Fridge, microwave, oven, stovetop
Charming 1913 3 Bedr / 2 Bath / Dutch Brick Haus / Living & Dining / New HVAC
10.0 out of 10, Exceptional, (62)
"This property was a wonderful place to stay for a fun girls weekend. It is centrally located and Paul was a gravious host. The house has everything you need including a nice bottle of wine and chocolate muffins. We would definitely stay here again"
Charming 1913 3 Bedr / 2 Bath / Dutch Brick Haus / Living & Dining / New HVAC
Exterior
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
9.8 out of 10, Exceptional, (30)
"Enjoyed our stay very much! The proximity of location to many different places was within walking distance. Thank you!"
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Fridge, microwave, oven, stovetop
Brick Bungalow
10.0 out of 10, Exceptional, (37)
"Great property! There were only a few minor things that didn't make this property perfect. It's smells musty when you first walk in (but it doesn't linger and didn't bother us throughout the stay). The master bed also seemed to slant a little. However, our backs weren't sore the next day, and we didn't end up rolling to the center, so I think it may just be an uneven floor. With that said, I didn't mention either to the host, but they were very good at communicating, and I think they would fix...
Brick Bungalow
Private kitchen
The Farmhouse Inn: 3 bed, 3.5 whole house rental
10.0 out of 10, Exceptional, (83)
"We really enjoyed the property. It was very clean and comfortable. Plenty of room. The location was good and the Trolly company would pick us up at our front door!"
The Farmhouse Inn: 3 bed, 3.5 whole house rental
Property grounds
Cozy custom-built cabin - Lakeside
10.0 out of 10, Exceptional, (27)
"My wife and i celebrated and incredible 24th wedding anniversary made even more spectacular by this elegant country escape. A special thanks goes out to our hosts who made our weekend so memorable. You can tell they put a lot of love and hard work into this remarkable little oasis in the trees."
Cozy custom-built cabin - Lakeside
Living area
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
9.8 out of 10, Exceptional, (36)
"This was the perfect place for our annual Mom and Daughters weekend! Great location, comfy suite, and everything was a breeze- we felt right at home!"
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
Fridge, microwave, oven, stovetop
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
10.0 out of 10, Exceptional, (138)
"Our family went to Hermann to celebrate my sister’s birthday. The house was great! We were able to each have a room (ceiling fans greatly appreciated!) and with multiple bathrooms, it made it easy for everyone to get ready! The dining room table was wonderful for playing cards during the rainy weather. It’s a quaint older home with nice updates in the kitchen and bathrooms. Thanks for a great weekend!"
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
Fridge, microwave, oven, coffee/tea maker
Guest House- Downtown Hermann (Sleeps 16) 3 Bedroom 2.5 Bath
9.6 out of 10, Exceptional, (13)
"Great place for a big family. Good location."
Guest House- Downtown Hermann (Sleeps 16) 3 Bedroom 2.5 Bath
1 bedroom, iron/ironing board, free WiFi, bed sheets
The Artists Suites, Jackson Pollock Suite
10.0 out of 10, Exceptional, (28)
"Loved our time at the Jackson Pollock suite!"
The Artists Suites, Jackson Pollock Suite
Iron/ironing board, WiFi, bed sheets
Cozy Riverview Cottage. 5 minute walk to downtown
10.0 out of 10, Exceptional, (11)
"Wonderful property will be going back soon."
The price is CA $273
CA $398 total
includes taxes & fees
May 20 - May 21
Cozy Riverview Cottage. 5 minute walk to downtown
Exterior
Get Away From It All! Escape To Peace And Quiet!
10.0 out of 10, Exceptional, (73)
"This was the perfect place for our family to gather. This property offered so many different activities for kids of all ages!"
Get Away From It All! Escape To Peace And Quiet!
Exterior
Newly remodeled home in Historic Hermann Wine Counrtry.
10.0 out of 10, Exceptional, (56)
"Great home. Comfortable. We had a wonderful time in Hermann"
The price is CA $615
CA $1,144 total
includes taxes & fees
May 15 - May 16
Newly remodeled home in Historic Hermann Wine Counrtry.
Terrace/patio
Gipfel Suite - Himmel Haus Bed & Breakfast
10.0 out of 10, Exceptional, (67)
"Enjoyed our stay. Great breakfast. Beautiful view from back deck"
The price is CA $135
CA $229 total
includes taxes & fees
May 21 - May 22
Gipfel Suite - Himmel Haus Bed & Breakfast
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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.

Other types of properties in Montgomery City you may be interested in

Indoor pool
Amerihost Inn & Suites - Mexico
2.5 star property
5.6 out of 10, (227)
"Very good pricing"
The price is CA $86
CA $98 total
includes taxes & fees
May 15 - May 16
Amerihost Inn & Suites - Mexico
Restaurant
Hermann Crown Suites
3.5 star property
9.4 out of 10, Exceptional, (572)
"Nice quiet area. Scenic Town with plenty to do. Staff at hotel very accommodating. Very homey feel. The rooms are a bit outdated. Need a bit of a makeover."
The price is CA $220
CA $252 total
includes taxes & fees
May 15 - May 16
Hermann Crown Suites
Exterior
Baymont by Wyndham Fulton
2.5 star property
8.4 out of 10, Very good, (735)
"Good hotel for travel stays."
The price is CA $138
CA $155 total
includes taxes & fees
May 20 - May 21
Baymont by Wyndham Fulton
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montgomery City. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! : This vacation home rental outside of Montgomery City offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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

While exploring the area, visit the sights like Graham Cave State Park, Hermannhof Vineyards, and Stone Hill Winery. Endless Summer Winery and Shrine of Our Lady of Sorrows 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.

Recent reviews of Montgomery City properties
Expedia verified reviews