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Montgomery City Vacation Rentals

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.
$230 nightly
The price is $246
Sep 27 - Sep 28
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.

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.
$194 nightly
The price is $202
Oct 18 - Oct 19
Total with taxes and fees
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
$195 nightly
The price is $210
Oct 27 - Oct 28
Total with taxes and fees
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.
$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!
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.
$149 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
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.
$323 nightly
The price is $347
Sep 28 - Sep 29
Total with taxes and fees
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
$194 nightly
The price is $223
Sep 27 - Sep 28
Total with taxes and fees
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
$73 nightly
The price is $80
Oct 22 - Oct 23
Total with taxes and fees
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.
$193 nightly
The price is $208
Sep 27 - Sep 28
Total with taxes and fees
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.
$195 nightly
The price is $212
Sep 27 - Sep 28
Total with taxes and fees
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
$245 nightly
The price is $257
Sep 27 - Sep 28
Total with taxes and fees
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.
$195 nightly
The price is $212
Sep 27 - Sep 28
Total with taxes and fees
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
$276 nightly
The price is $314
Sep 27 - Sep 28
Total with taxes and fees
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.
$247 nightly
The price is $264
Sep 29 - Sep 30
Total with taxes and fees
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.
$247 nightly
The price is $264
Oct 13 - Oct 14
Total with taxes and fees
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.
$273 nightly
The price is $298
Sep 27 - Sep 28
Total with taxes and fees
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
$247 nightly
The price is $264
Oct 6 - Oct 7
Total with taxes and fees
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
$68 nightly
The price is $76
Oct 19 - Oct 20
Total with taxes and fees
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
$182 nightly
The price is $206
Sep 27 - Sep 28
Total with taxes and fees
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.
$292 nightly
The price is $332
Sep 27 - Sep 28
Total with taxes and fees
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 12 hours ago
Captain Wohlt Inn Bed & Breakfast

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 $76 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 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.