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Montgomery City Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Montgomery City vacation rentals

A covered patio with a table and chairs, a grill, and a view of a grassy yard.

1. Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (49 reviews)
"Very nice place "
United States
Yaqui S.
The price is ￥28,310
￥38,643 total
includes taxes & fees
Sep 28 - Sep 29
Secluded 2 bedroom home close to Hermann
A laundry area with washing machines, a wooden cabinet, and a bar stool area.

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

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (4 reviews)
"Overall stay was amazing! The property was just like described and the hostess was easy to communicate with."
United States
Prisilla B.
The price is ￥18,244
￥31,841 total
includes taxes & fees
Oct 18 - Oct 19
Papa's Cabin - 40 acres & 5 acre lake!
A compact living space with a sofa, a TV, a kitchen area with a fridge, microwave, and coffee maker, and a dining table.

3. The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (37 reviews)
"It’s an absolute must do! Such a cool little town right on the Katy Trail!"
United States
Weston
The price is ￥30,676
￥32,970 total
includes taxes & fees
Oct 27 - Oct 28
The Mercantile on the Katy Trail
A wooden deck with a view of a lake, a grill, and a covered seating area.

4. Country Container Tiny House. Experience peace by the water & native wildlife!

Country Container Tiny House. Experience peace by the water & native wildlife!
Fulton
10.0 out of 10, Exceptional, (37 reviews)
"Great little place to stay and unwind. Very peaceful and quiet."
United States
craig p.
The price is ￥18,087
￥25,580 total
includes taxes & fees
Oct 25 - Oct 26
Country Container Tiny House. Experience peace by the water & native wildlife!
An outdoor patio with a pergola, wicker furniture, and a view of the landscape.

5. Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (137 reviews)
"Everything was wonderful! It was a great room, a beautiful view from the terrace and a great breakfast."
United States
Kristin V.
The price is ￥15,571
￥25,459 total
includes taxes & fees
Sep 29 - Sep 30
Gipfel Suite - Himmel Haus Bed & Breakfast
A spacious living area with a large blue sofa, a television, and a wooden entertainment unit.

6. 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, (15 reviews)
"Host was very accommodating, property perfect, I can't say enough good things about our stay."
United States
Susan R.
The price is ￥31,849
￥54,518 total
includes taxes & fees
Sep 28 - Sep 29
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
A room with a blue sofa, a small round rug, a table with a lamp, and a window with a view of greenery.

7. The Cottage

The Cottage
2.0 star property
Hermann
The price is ￥33,559
￥38,584 total
includes taxes & fees
Oct 28 - Oct 29
The Cottage
A spacious room with a dining area, a fireplace, a television, and a staircase leading to an upper level.

8. Kingdom City, MO| King bed|Smoking

Kingdom City, MO| King bed|Smoking
Kingdom City, MO
10.0 out of 10, Exceptional, (36 reviews)
"I found it very easy to get around Kingdom City from this spot. Convenient access nearby for food or gas as well."
United States
Anonymous traveler
The price is ￥9,870
￥12,631 total
includes taxes & fees
Oct 22 - Oct 23
Kingdom City, MO| King bed|Smoking
A living room with a brick wall, wooden flooring, a sofa, a coffee table, and a television.

9. Large Unique 2-Bedroom Gamed Themed Loft

Large Unique 2-Bedroom Gamed Themed Loft
Fulton
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay! We have stayed here several times and it’s always been great! "
United States
chris w.
The price is ￥17,694
￥32,779 total
includes taxes & fees
Sep 28 - Sep 29
Large Unique 2-Bedroom Gamed Themed Loft
A compact kitchen with a bar area, a dining table with stools, and a small seating area with two chairs.

10. Wine Alley East suite

Wine Alley East suite
Hermann
9.4 out of 10, Exceptional, (86 reviews)
"Host was great. Easy checkin and checkout. Great location to ride trolley to wineries and then walk Hermann at night."
United States
Sandy H.
The price is ￥22,806
￥33,415 total
includes taxes & fees
Sep 28 - Sep 29
Wine Alley East suite
A wooden staircase leading to a modern building with large windows, surrounded by trees and gravel.

11. Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
Hermann
10.0 out of 10, Exceptional, (7 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 ￥27,524
￥40,350 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
A compact kitchen with a wooden countertop and stools, a dark sofa, and two armchairs in a living area with hardwood flooring.

12. Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (58 reviews)
"Great location for the price compared to others in the area! Very walkable. Parking was accessible and the host was helpful."
United States
Laurend M.
The price is ￥22,806
￥33,415 total
includes taxes & fees
Sep 28 - Sep 29
Wine Alley West Suite
A living room with a wooden floor, a dining area with a table and chairs, a patterned armchair, a small table with a lamp, and a potted plant.

13. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.8 out of 10, Exceptional, (17 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥27,524
￥49,414 total
includes taxes & fees
Sep 28 - Sep 29
Charming 2-bedroom house in fabulous downtown Hermann
A building with large windows, a covered porch, and a welcome mat.

14. 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 ￥35,671
￥41,482 total
includes taxes & fees
Sep 29 - Sep 30
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
A building with large windows, a covered porch, and a welcome mat.

15. 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 ￥35,671
￥41,482 total
includes taxes & fees
Oct 13 - Oct 14
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
A bedroom with a bed, two bedside tables, a mirror, a wooden door, and a nightstand with a plant.

16. In town -2 bedroom + 2 sofa beds + game room/common area -fits 8 people

In town -2 bedroom + 2 sofa beds + game room/common area -fits 8 people
Hermann
9.6 out of 10, Exceptional, (8 reviews)
"Angela has a very clean and spacious basement rental that was perfect for our weekend ! The home was clean, bright and very well cared for. We definitely recommend it for your family."
United States
Sheryl C.
The price is ￥24,064
￥46,906 total
includes taxes & fees
Sep 28 - Sep 29
In town -2 bedroom + 2 sofa beds + game room/common area -fits 8 people
A modern kitchen with a marble backsplash, stainless steel appliances, and a wooden bar area with bar stools.

17. 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 ￥35,671
￥41,482 total
includes taxes & fees
Oct 6 - Oct 7
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

18. King Bed Non-Smoking

King Bed Non-Smoking
Fulton, MO
10.0 out of 10, Exceptional, (93 reviews)
"Location is close to local attractions but not busy or noisy."
United States
Anonymous traveler
The price is ￥9,775
￥11,936 total
includes taxes & fees
Oct 18 - Oct 19
King Bed Non-Smoking
A hallway with a chalkboard, a bench, a colorful rug, and shelves with papers.

19. Germantown Inn & Lounge RM 3

Germantown Inn & Lounge RM 3
Hermann
The price is ￥25,479
￥32,440 total
includes taxes & fees
Sep 28 - Sep 29
Germantown Inn & Lounge RM 3
A brick building with a red and white facade, a sign reading 'Ash Creek Suite', and outdoor seating with tables and chairs.

20. Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann
Hermann
9.4 out of 10, Exceptional, (56 reviews)
"Great place! Great location! And clean!"
United States
Cheryl E.
The price is ￥31,456
￥52,285 total
includes taxes & fees
Sep 28 - Sep 29
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

Captain Wohlt Inn Bed & Breakfast

Captain Wohlt Inn Bed & Breakfast

8/10 Good
"The property had a very laid back and relaxed environment. The property owner was very informative about the area and provided some helpful tips for local businesses."
Steve 1-night trip
Posted 21 hours ago
Captain Wohlt Inn Bed & Breakfast

Find out more about Montgomery City

Search for holiday rentals in Montgomery City on Expedia! You can easily find your home rentals, villas, holiday apartments in Montgomery City using one of the methods below:

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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?

Cozy Riverview Cottage. 5 minute walk to downtown: This vacation home rental outside of Montgomery City is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. 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.