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Montgomery City Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montgomery City vacation rentals

A compact living space with a sofa, a TV, a kitchen area with a fridge, microwave, and coffee maker, and a dining table.

1. The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (38 reviews)
"It’s an absolute must do! Such a cool little town right on the Katy Trail!"
United States
Weston
$195 nightly
The price is $210
Oct 27 - Oct 28
Total with taxes and fees
The Mercantile on the Katy Trail
Private kitchen

2. The Cottage

The Cottage
2.0 star property
Hermann
$177 nightly
The price is $204
Oct 6 - Oct 7
Total with taxes and fees
The Cottage
A covered patio with a table and chairs, a grill, and a view of a grassy yard.

3. Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (50 reviews)
"Very nice place "
United States
Yaqui S.
$237 nightly
The price is $253
Oct 6 - Oct 7
Total with taxes and fees
Secluded 2 bedroom home close to Hermann
A laundry area with washing machines, a wooden cabinet, and a bar stool area.

4. 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.
$197 nightly
The price is $205
Oct 18 - Oct 19
Total with taxes and fees
Papa's Cabin - 40 acres & 5 acre lake!
A spacious living area with a large blue sofa, a television, and a wooden entertainment unit.

5. 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, (17 reviews)
"Host was very accommodating, property perfect, I can't say enough good things about our stay."
United States
Susan R.
$395 nightly
The price is $422
Oct 7 - Oct 8
Total with taxes and fees
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
A compact kitchen with a bar area, a dining table with stools, and a small seating area with two chairs.

6. 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.
$200 nightly
The price is $217
Oct 6 - Oct 7
Total with taxes and fees
Wine Alley East suite
A building with large windows, a covered porch, and a welcome mat.

7. 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.
$256 nightly
The price is $273
Oct 20 - Oct 21
Total with taxes and fees
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
A wooden deck with a view of a lake, a grill, and a covered seating area.

8. 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.
$150 nightly
The price is $163
Oct 25 - Oct 26
Total with taxes and fees
Country Container Tiny House. Experience peace by the water & native wildlife!
A bedroom with a bed, bedside lamps, a ceiling fan, a window with curtains, a wall-mounted TV, and a radiator.

9. Germantown Inn & Lounge RM 1

Germantown Inn & Lounge RM 1
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"We had a very pleasant stay. From check in, to check out, it was all perfect!"
United States
Jennifer A.
$233 nightly
The price is $264
Oct 6 - Oct 7
Total with taxes and fees
Germantown Inn & Lounge RM 1
A bed with a quilted cover, a brick wall, and a window with curtains.

10. Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery

Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery
Hermann
10.0 out of 10, Exceptional, (2 reviews)
"Great location, very clean, comfy bed. Only downside was the tiny bathroom and tub with no standup shower but we knew that going into it. Still a great place to stay!!"
United States
Erica L.
$318 nightly
The price is $360
Nov 1 - Nov 2
Total with taxes and fees
Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery
A building with large windows, a covered porch, and a welcome mat.

11. 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.
$256 nightly
The price is $273
Oct 13 - Oct 14
Total with taxes and fees
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
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.
$200 nightly
The price is $217
Oct 6 - Oct 7
Total with taxes and fees
Wine Alley West Suite
A brick building with a sign that reads "MUNHART'S." There are outdoor tables and chairs, and a covered patio area.

13. Plenty room for relaxing and downtown location to walk around!

Plenty room for relaxing and downtown location to walk around!
Hermann
10.0 out of 10, Exceptional, (21 reviews)
"We loved the room and enjoyed all of the amenities and small touches. The location is fantastic and centralized in the Herman area. We highly recommend it."
United States
Joe
$263 nightly
The price is $297
Nov 2 - Nov 3
Total with taxes and fees
Plenty room for relaxing and downtown location to walk around!
A bedroom with a bed, a bedside table, a mirror, an air conditioning unit, and a window with curtains.

14. Suite, 2 King Beds, 1 Bath, Sleeps 4, Downtown Hermann at Lionheart Whiskey Co. a Missouri Distillery

Suite, 2 King Beds, 1 Bath, Sleeps 4, Downtown Hermann at Lionheart Whiskey Co. a Missouri Distillery
Hermann
$372 nightly
The price is $420
Nov 1 - Nov 2
Total with taxes and fees
Suite, 2 King Beds, 1 Bath, Sleeps 4, Downtown Hermann at Lionheart Whiskey Co. a Missouri Distillery
A wooden staircase leading to a modern building with large windows, surrounded by trees and gravel.

15. 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, (8 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
$257 nightly
The price is $269
Oct 11 - Oct 12
Total with taxes and fees
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
A hallway with a chalkboard, a bench, a colorful rug, and shelves with papers.

16. Germantown Inn & Lounge RM 5

Germantown Inn & Lounge RM 5
Hermann
$186 nightly
The price is $210
Oct 6 - Oct 7
Total with taxes and fees
Germantown Inn & Lounge RM 5
A brick building with a red and white facade, a sign reading 'Ash Creek Suite', and outdoor seating with tables and chairs.

17. 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.
$309 nightly
The price is $349
Oct 6 - Oct 7
Total with taxes and fees
Ash Creek Suite - In Downtown Historic Hermann
A modern kitchen with a marble backsplash, stainless steel appliances, and a wooden bar area with bar stools.

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

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Hermann
$257 nightly
The price is $274
Oct 13 - Oct 14
Total with taxes and fees
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
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.

19. 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
$292 nightly
The price is $330
Oct 6 - Oct 7
Total with taxes and fees
Charming 2-bedroom house in fabulous downtown Hermann
A black door with a welcome sign, a stone wall, and a wooden post with the number 139.

20. 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, (66 reviews)
"Loved this stay for our girls trip!! So nice and clean! Would definitely rent again!"
United States
Lauren
$480 nightly
The price is $543
Oct 11 - Oct 12
Total with taxes and fees
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
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

Holiday Inn Express & Suites Kingdom City by IHG

Holiday Inn Express & Suites Kingdom City by IHG

10/10 Excellent
"Hotel was great. Once again I had issues with Hotels.com. Booked a king room (higher rate) and when I checked in was given a two queen room When I said I paid higher for a king room they left the charge the same and said “you booked through a third party company” So I got a lesser room at a higher rate. I am done with this app. I have used it many times and here lately it has failed me more times than it should."
Cory 1-night trip
Posted 17 hours ago
Holiday Inn Express & Suites Kingdom City by IHG

Find out more about Montgomery City

Everything you need to know about Montgomery City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery City vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery City vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery City. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montgomery City in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $73 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montgomery City rentals

At Expedia, we put the best Montgomery City vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montgomery City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery City vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Katy Trail - McKittrick Trailhead are a couple of picturesque spots to get outside and enjoy nature. 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.