Montgomery City Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 20 - Jul 21
Tomorrow
Jul 21 - Jul 22
Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3

Vacation Rentals in Montgomery City

The Mercantile on the Katy Trail
Welcome to our hotel, where guests can enter through the main entrance, flanked by two potted plants.

The Mercantile on the Katy Trail

4.5 star property
10.0 out of 10, Exceptional, (17)
"Nice quiet area with open concept space inside."
The price is CA $271
CA $290 total
includes taxes & fees
Jul 22 - Jul 23
The Mercantile on the Katy Trail
Gipfel Suite - Himmel Haus Bed & Breakfast
Relax in this serene outdoor space with a round table and four chairs, surrounded by lush greenery and a beautiful view.

Gipfel Suite - Himmel Haus Bed & Breakfast

10.0 out of 10, Exceptional, (103)
"1st time in Hermann and loved our stay. Very clean and hospitable and peaceful "
The price is CA $136
CA $230 total
includes taxes & fees
Jul 28 - Jul 29
Gipfel Suite - Himmel Haus Bed & Breakfast
The Artists Suites, Leonardo da Vinci Suite
Guests can enjoy a relaxing stay in this charming two-story home with a cozy porch and outdoor seating area.

The Artists Suites, Leonardo da Vinci Suite

9.8 out of 10, Exceptional, (45)
"The room was nice, close to everything. "
The price is CA $122
CA $222 total
includes taxes & fees
Jul 21 - Jul 22
The Artists Suites, Leonardo da Vinci Suite
The Artists Suites, Vincent Van Gogh Suites
Enjoy a rustic retreat with a garage, porch, and outdoor seating area.

The Artists Suites, Vincent Van Gogh Suites

9.8 out of 10, Exceptional, (29)
"Highly recommend! Easy check in and great location."
The price is CA $122
CA $222 total
includes taxes & fees
Jul 21 - Jul 22
The Artists Suites, Vincent Van Gogh Suites
Wine Alley East suite
Enjoy cooking in this well-equipped kitchen with a central island, sink, and microwave above the oven.

Wine Alley East suite

9.4 out of 10, Exceptional, (68)
"Great location "
The price is CA $199
CA $291 total
includes taxes & fees
Jul 21 - Jul 22
Wine Alley East suite
The Artists Suites, Jackson Pollock Suite
Relax in a cozy corner with a comfortable armchair, small table, and plush throw blanket.

The Artists Suites, Jackson Pollock Suite

9.8 out of 10, Exceptional, (52)
"We came for the antique show. We enjoyed the the entire package that Hermann offers. Wine, Brew, Music and food. It did not disappoint. "
The price is CA $122
CA $201 total
includes taxes & fees
Jul 21 - Jul 22
The Artists Suites, Jackson Pollock Suite
Cozy Riverview Cottage. 5 minute walk to downtown
Cozy retreat with a large bed, ceiling fan, and a bedside table with a lamp.

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (28)
"Was such a cute cottage! We had a wonderful stay and it was just as described! I would definitely stay there again. "
The price is CA $247
CA $365 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Riverview Cottage. 5 minute walk to downtown
Your home away from home! The Branson Country B&B in Hermann,Mo
Relax on the deck with comfortable seating and a shaded table.

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

9.8 out of 10, Exceptional, (54)
"We had a nice weekend at this nice place. "
The price is CA $412
CA $520 total
includes taxes & fees
Jul 21 - Jul 22
Your home away from home! The Branson Country B&B in Hermann,Mo
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Relax in a traditional room with a unique metal swing chair and large window.

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (98)
"Great stay . Perfect for 3 couples. House was exactly as described with a great location. Would 100% stay here again! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
The House on Wine Alley
Cozy living space with a kitchenette, dining area, and comfortable seating for relaxation.

The House on Wine Alley

9.0 out of 10, Wonderful, (44)
"Great place to stay in the heart of Hermann! Definitely recommend!"
The price is CA $316
CA $441 total
includes taxes & fees
Jul 21 - Jul 22
The House on Wine Alley
The Artists Suites, Claude Monet Suite
Staircase leads to the entrance of Artist Suites.

The Artists Suites, Claude Monet Suite

10.0 out of 10, Exceptional, (42)
"Beautiful room right next to great night life atmosphere!"
The price is CA $122
CA $222 total
includes taxes & fees
Jul 21 - Jul 22
The Artists Suites, Claude Monet Suite
Downtown Location, Door to Door Private Shuttle, Great View, & Free Breakfasts
Enjoy cocktails and social gatherings in this stylish space with a bar area, dining table, and comfortable seating.

Downtown Location, Door to Door Private Shuttle, Great View, & Free Breakfasts

9.6 out of 10, Exceptional, (84)
"Great for our stay."
The price is CA $433
CA $557 total
includes taxes & fees
Jul 21 - Jul 22
Downtown Location, Door to Door Private Shuttle, Great View, & Free Breakfasts
Ash Creek Suite - In Downtown Historic Hermann
Cozy retreat with a dining area, kitchenette, and television.

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (48)
"We went down for a wedding. The little cottage was perfect for us. I really enjoyed being able to sit on the little patio. "
The price is CA $172
CA $345 total
includes taxes & fees
Jul 24 - Jul 25
Ash Creek Suite - In Downtown Historic Hermann
Cottage Properties - Country Log Cabin
Cozy space with a high ceiling, wooden beams, and a fireplace.

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (163)
"Had a great time! "
Cottage Properties - Country Log Cabin
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Relax by the serene pool surrounded by lush greenery and a charming wooden bench.

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

8.8 out of 10, Excellent, (16)
"We had a great time at this location. It was cute, clean, and well maintained."
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
Cozy living space with a dining area, television, and exposed brick walls.

Suite #4 - Adorable 2 Bed Suite in Downtown Hermann

10.0 out of 10, Exceptional, (52)
"Cute little suite- great location!!"
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
Kitchen features a double oven, microwave, and dishwasher, with a window above the sink and a countertop with various kitchen items.

The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

10.0 out of 10, Exceptional, (160)
"This property was nicely updated. There was plenty of space for 6 adults. The bathrooms were very nice and clean. The location was great!"
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
Cozy custom-built Cabin - Lakeside
Relax in style with Adirondack chairs and a barbecue grill, perfect for socializing or a quiet moment.

Cozy custom-built Cabin - Lakeside

10.0 out of 10, Exceptional, (53)
"Super cute little cabin with a great atmosphere, cute and homey feel with an amazing view"
Cozy custom-built Cabin - Lakeside
Glamping with gorgeous sunset views, trolley to all wineries
Enjoy cooking in this well-equipped kitchen with a black stove top, sink, coffee maker, and microwave.

Glamping with gorgeous sunset views, trolley to all wineries

10.0 out of 10, Exceptional, (3)
"It was a wonderful stay for 5 of us girls going to Herman for a day at the Winery. This location was perfect, just 7 minutes up the road from Downtown Herman. The trolley picked us up with no issue. Very quiet location, perfect for a quick getaway!"
The price is CA $206
CA $316 total
includes taxes & fees
Jul 21 - Jul 22
Glamping with gorgeous sunset views, trolley to all wineries
Wine Alley West Suite
Cozy living space with a kitchen area, bar counter, and stools.

Wine Alley West Suite

9.0 out of 10, Wonderful, (43)
"Great location and host. "
The price is CA $199
CA $291 total
includes taxes & fees
Jul 21 - Jul 22
Wine Alley West Suite
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montgomery City Hotel Reviews

Best Western Teal Lake Inn

Best Western Teal Lake Inn

10/10 Excellent
"Simply clean and tidy. Nice and friendly staff"
Tim 1-night trip
Posted 11 hours ago
Best Western Teal Lake Inn

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?

Gipfel Suite - Himmel Haus Bed & Breakfast: This vacation home rental outside of Montgomery City is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a microwave.

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. Stone Hill Winery 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.