Montgomery City Vacation Rentals

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Our top choices for Montgomery City vacation rentals

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, (7 reviews)
"The home was very clean and had everything we needed. Very quiet area out in the country. Enjoyed our stay there and would highly recommend staying there."
United States
Sheri D.
$342 nightly
The price is $356
Feb 13 - Feb 14
Total with taxes and fees
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

Archie’s House

Archie’s House
Berger
10.0 out of 10, Exceptional, (36 reviews)
"Archie’s Place was great for a quick weekend in Hermann for Octoberfest. We were only 5-10 minutes from Hermann, and it was a nice, quiet place."
United States
Anonymous traveler
$421 nightly
The price is $421
Feb 12 - Feb 13
Total with taxes and fees
Archie’s House

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (28 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
$214 nightly
The price is $230
Feb 17 - Feb 18
Total with taxes and fees
The Mercantile on the Katy Trail

The Pollock Suite is one of our four rooms.

The Pollock Suite is one of our four rooms.
Hermann
9.8 out of 10, Exceptional, (68 reviews)
"Great location, plenty of amenities, gracious host, shops and restaurants immediately nearby"
United States
Brandon R.
$181 nightly
The price is $205
Feb 15 - Feb 16
Total with taxes and fees
The Pollock Suite is one of our four rooms.

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 $284
Feb 17 - Feb 18
Total with taxes and fees
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

Cozy Riverview Cottage. 5 minute walk to downtown

Cozy Riverview Cottage. 5 minute walk to downtown
Hermann
9.8 out of 10, Exceptional, (45 reviews)
"Adorable little cottage that has a rustic feel to it. Perfect for a couples getaway. Hosts had excellent communication. "
United States
Terri B.
$240 nightly
The price is $266
Feb 12 - Feb 13
Total with taxes and fees
Cozy Riverview Cottage. 5 minute walk to downtown

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
$257 nightly
The price is $269
Feb 12 - Feb 13
Total with taxes and fees
Nature`s Nook by Zia, Hermann

Downtown Hermann Vacation Home Near Wineries!

Downtown Hermann Vacation Home Near Wineries!
3.0 star property
Hermann
10.0 out of 10, Exceptional, (1 review)
"This is a very cute little house on the end of a quiet street. It's within easy walking distance of all the shops, restaurants, wineries, distilleries, and bars between 1st Street and 5th Street. If you don't mind a longer, hillier walk you could also go further south to City Park or to Stone Hill winery. But there's also easy transportation on the Trolley or local ride services. We were happy to find there were more beds than pictured (3 queen size downstairs between 2 bedrooms, and 2 queens...
United States
Tara
$602 nightly
The price is $688
Feb 12 - Feb 13
Total with taxes and fees
Downtown Hermann Vacation Home Near Wineries!

Ash Creek Guesthouse - Downtown Historic Hermann

Ash Creek Guesthouse - Downtown Historic Hermann
Hermann
9.8 out of 10, Exceptional, (47 reviews)
"Great!!"
United States
Robert S.
$333 nightly
The price is $377
Feb 12 - Feb 13
Total with taxes and fees
Ash Creek Guesthouse - Downtown Historic Hermann

Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (114 reviews)
"Nice property, with great view of Hermann"
United States
Mike L.
$149 nightly
The price is $168
Feb 16 - Feb 17
Total with taxes and fees
Gipfel Suite - Himmel Haus Bed & Breakfast

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, (17 reviews)
"Quick weekend trip to Hermann, Laura was a fantastic host. Would definitely stay again, she was very accommodating!"
United States
Brent K.
$165 nightly
The price is $186
Feb 12 - Feb 13
Total with taxes and fees
Plenty room for relaxing and downtown location to walk around!

Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
10.0 out of 10, Exceptional, (5 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
$235 nightly
The price is $266
Feb 12 - Feb 13
Total with taxes and fees
Charming 2-bedroom house in fabulous downtown Hermann

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 $284
Feb 17 - Feb 18
Total with taxes and fees
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

The House on Wine Alley

The House on Wine Alley
Hermann
9.0 out of 10, Wonderful, (55 reviews)
"Parking was a little difficult but decent place to stay"
United States
Kim W.
$423 nightly
The price is $451
Feb 14 - Feb 15
Total with taxes and fees
The House on Wine Alley

Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!

Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
Hermann
10.0 out of 10, Exceptional, (20 reviews)
"Well furnished "
United States
Toby J.
$284 nightly
The price is $320
Feb 17 - Feb 18
Total with taxes and fees
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!

Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann

Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann
Hermann
8.8 out of 10, Excellent, (8 reviews)
"We stayed here and were very impressed with the cleanliness and the extra amenities provided and the access to additional if needed in the barn! "
United States
Shannon O.
$256 nightly
The price is $284
Feb 17 - Feb 18
Total with taxes and fees
Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann

Kork Haus - Whole house rental in Downtown Hermann

Kork Haus - Whole house rental in Downtown Hermann
Hermann
9.6 out of 10, Exceptional, (25 reviews)
"Great location, easy walking distance to downtown! "
United States
Cheryl M.
$333 nightly
The price is $377
Feb 12 - Feb 13
Total with taxes and fees
Kork Haus - Whole house rental in Downtown Hermann

The Da Vinci Suite is one of our four rooms.

The Da Vinci Suite is one of our four rooms.
Hermann
9.8 out of 10, Exceptional, (54 reviews)
"Great location, cool place"
United States
Dave J.
$182 nightly
The price is $206
Feb 12 - Feb 13
Total with taxes and fees
The Da Vinci Suite is one of our four rooms.

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

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Hermann
$256 nightly
The price is $284
Feb 17 - Feb 18
Total with taxes and fees
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

Spacious House walking distance from downtown Hermann

Spacious House walking distance from downtown Hermann
Hermann
10.0 out of 10, Exceptional, (22 reviews)
"Very nice home inside, hardwood floors, spacious, open living room-dining room area, nice deck. Water pressure in the showers is AMAZING! Coffee bar is nice too. "
United States
Lynne G.
$611 nightly
The price is $661
Feb 12 - Feb 13
Total with taxes and fees
Spacious House walking distance from downtown 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

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 $168 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.

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?

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!: This vacation home rental outside of Montgomery City is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.