Montgomery City Vacation Rentals

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Our top choices for Montgomery City vacation rentals

Archie’s House

Archie’s House
Berger
10.0 out of 10, Exceptional, (36 reviews)
"Cutest house! Very well kept and clean! Exceeded expectations and would definitely stay again if we were ever in the area! Thanks for a great stay! "
United States
Jennifer S.
The price is CA $539
CA $727 total
includes taxes & fees
May 26 - May 27
Archie’s House

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
9.8 out of 10, Exceptional, (11 reviews)
"Great place to ring in the New Year under clear skies where you could see all the stars "
United States
Nicholas N.
The price is CA $280
CA $507 total
includes taxes & fees
May 26 - May 27
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (30 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
The price is CA $280
CA $301 total
includes taxes & fees
Jun 2 - Jun 3
The Mercantile on the Katy Trail

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

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay at the cabin!! So much space to spread out inside, and the property & lake are so peaceful and enjoyable to explore. Though we only spent one night, we really loved it there, and will definitely be back when we are in the area visiting family!"
United States
Scott V.
The price is CA $167
CA $290 total
includes taxes & fees
Jun 2 - Jun 3
Papa's Cabin - 40 acres & 5 acre lake!

Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
The price is CA $249
CA $351 total
includes taxes & fees
May 26 - May 27
Secluded 2 bedroom home close to Hermann

The Laughing Boar, perfectly located downtown

The Laughing Boar, perfectly located downtown
Hermann
10.0 out of 10, Exceptional, (57 reviews)
"Great house and location. Would stay here again. "
United States
Valarie H.
The price is CA $553
CA $959 total
includes taxes & fees
May 26 - May 27
The Laughing Boar, perfectly located downtown

Newly remodeled home in Historic Hermann Wine Counrtry.

Newly remodeled home in Historic Hermann Wine Counrtry.
Hermann
10.0 out of 10, Exceptional, (81 reviews)
"Home was very clean and spacious with everything we needed available! "
United States
Rhonda I.
The price is CA $618
CA $1,140 total
includes taxes & fees
May 26 - May 27
Newly remodeled home in Historic Hermann Wine Counrtry.

Ash Creek Guesthouse - Downtown Historic Hermann

Ash Creek Guesthouse - Downtown Historic Hermann
Hermann
9.8 out of 10, Exceptional, (48 reviews)
"Host was great!"
United States
Christy C.
The price is CA $311
CA $566 total
includes taxes & fees
May 26 - May 27
Ash Creek Guesthouse - Downtown Historic Hermann

Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (51 reviews)
"Close to everything downtown. Reasonable price. We were gone most of the time so we just needed a place to sleep. Parking was a slight issue as there were 4 cars crammed into a steep lot with uneven ground. It met our needs and we would like to return."
United States
Steven
The price is CA $200
CA $298 total
includes taxes & fees
May 26 - May 27
Wine Alley West Suite

7th Heaven Guesthouse

7th Heaven Guesthouse
Hermann
10.0 out of 10, Exceptional, (36 reviews)
"Host was very welcoming and responsive before and during our stay. The place has amazing views and plenty of rooms and bathrooms for 4 couples to be very comfortable. Thank you for all the wonderful hospitality!"
United States
Mary Jo T.
The price is CA $529
CA $1,017 total
includes taxes & fees
May 26 - May 27
7th Heaven Guesthouse

Your home away from home! The Branson Country B&B in Hermann,Mo

Your home away from home! The Branson Country B&B in Hermann,Mo
Hermann
9.6 out of 10, Exceptional, (61 reviews)
"Beautiful home we will stay again when in the area. "
United States
Jeannie C.
The price is CA $415
CA $531 total
includes taxes & fees
May 26 - May 27
Your home away from home! The Branson Country B&B in Hermann,Mo

Spacious House walking distance from downtown Hermann

Spacious House walking distance from downtown Hermann
Hermann
10.0 out of 10, Exceptional, (23 reviews)
"House was great for our large group celebrating a bride"
United States
Stephanie M.
The price is CA $311
CA $680 total
includes taxes & fees
May 26 - May 27
Spacious House walking distance from downtown Hermann

The House on Wine Alley

The House on Wine Alley
Hermann
9.0 out of 10, Wonderful, (56 reviews)
"Loved the house. Perfect location! Had everything we needed for us 3 girls! Will definitely book again!"
United States
Stacey M.
The price is CA $318
CA $451 total
includes taxes & fees
May 26 - May 27
The House on Wine Alley

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is CA $313
CA $393 total
includes taxes & fees
May 26 - May 27
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

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 CA $313
CA $393 total
includes taxes & fees
May 26 - May 27
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

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 CA $242
CA $368 total
includes taxes & fees
May 26 - May 27
Nature`s Nook by Zia, Hermann

Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
Hermann
10.0 out of 10, Exceptional, (57 reviews)
"Great place to stay"
United States
Adam
The price is CA $325
CA $682 total
includes taxes & fees
May 26 - May 27
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

Kork Haus - Whole house rental in Downtown Hermann

Kork Haus - Whole house rental in Downtown Hermann
Hermann
9.6 out of 10, Exceptional, (26 reviews)
"Nice location!"
United States
Brian P.
The price is CA $311
CA $572 total
includes taxes & fees
Jun 2 - Jun 3
Kork Haus - Whole house rental in Downtown Hermann

Wine Alley East suite

Wine Alley East suite
Hermann
9.2 out of 10, Wonderful, (79 reviews)
"Great location "
United States
Scotti
The price is CA $200
CA $298 total
includes taxes & fees
May 26 - May 27
Wine Alley East suite

Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann
Hermann
9.4 out of 10, Exceptional, (54 reviews)
"Great area, close to everything. House was perfect"
United States
ELIZABETH K.
The price is CA $221
CA $407 total
includes taxes & fees
May 26 - May 27
Ash Creek Suite - In Downtown Historic Hermann
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

Find out more about Montgomery City

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 you're exploring the area, Graham Cave State Park and The Pinnacle are a couple of picturesque spots to get outside and enjoy nature. New Florence United Methodist Church and Endless Summer Winery 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.