Montgomery City Vacation Rentals

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Our top choices for Montgomery City vacation rentals

Smart TV
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

Vacation Home in Hermann

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
9.4 out of 10, Exceptional, (6)
"If you want seclusion and rural atmosphere, this is the property for you! No light pollution, you can see all the stars!"
United States
marlinVX
$302 nightly
The price is $313
Jan 6 - Jan 7
Total with taxes and fees
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Dining
Archie’s House

Vacation Home in Berger

Archie’s House
10.0 out of 10, Exceptional, (36)
"Everything was very nice!!! I highly recommend. "
United States
Mary T.
$409 nightly
The price is $409
Jan 5 - Jan 6
Total with taxes and fees
Archie’s House
Front of property
The Mercantile on the Katy Trail

Aparthotel in Hermann

The Mercantile on the Katy Trail
4.5 star property
9.8 out of 10, Exceptional, (28)
"Great place, fully stocked and clean!"
United States
Lauren
$214 nightly
The price is $230
Jan 6 - Jan 7
Total with taxes and fees
The Mercantile on the Katy Trail
Outdoor dining
Gipfel Suite - Himmel Haus Bed & Breakfast

Vacation Home in Hermann

Gipfel Suite - Himmel Haus Bed & Breakfast
10.0 out of 10, Exceptional, (114)
"This place was honestly the best part of our trip.It was clean, had all the amenities, and the breakfast was amazing. Renee was super sweet and easy to communicate with. "
United States
Erin W.
$149 nightly
The price is $168
Jan 5 - Jan 6
Total with taxes and fees
Gipfel Suite - Himmel Haus Bed & Breakfast
Outdoor dining
The Monet Suite is one of our four rooms.

Aparthotel in Hermann

The Monet Suite is one of our four rooms.
10.0 out of 10, Exceptional, (56)
"Very nice suite. Excellent location. Host was very friendly!"
United States
Eric R.
$182 nightly
The price is $206
Jan 5 - Jan 6
Total with taxes and fees
The Monet Suite is one of our four rooms.
Dining
Nature`s Nook by Zia, Hermann

Apartment in Hermann

Nature`s Nook by Zia, Hermann
10.0 out of 10, Exceptional, (3)
"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
Jan 5 - Jan 6
Total with taxes and fees
Nature`s Nook by Zia, Hermann
Dining
Ash Creek Suite - In Downtown Historic Hermann

Vacation Home in Hermann

Ash Creek Suite - In Downtown Historic Hermann
9.4 out of 10, Exceptional, (51)
"Met our needs"
United States
Craig C.
$219 nightly
The price is $248
Jan 5 - Jan 6
Total with taxes and fees
Ash Creek Suite - In Downtown Historic Hermann
Exterior detail
Plenty room for relaxing and downtown location to walk around!

Apartment in Hermann

Plenty room for relaxing and downtown location to walk around!
10.0 out of 10, Exceptional, (17)
"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
Jan 5 - Jan 6
Total with taxes and fees
Plenty room for relaxing and downtown location to walk around!
Exterior
Charming 2-bedroom house in fabulous downtown Hermann

Vacation Home in Hermann

Charming 2-bedroom house in fabulous downtown Hermann
10.0 out of 10, Exceptional, (4)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
$231 nightly
The price is $262
Jan 5 - Jan 6
Total with taxes and fees
Charming 2-bedroom house in fabulous downtown Hermann
Outdoor dining
Secluded 2 bedroom home close to Hermann

Vacation Home in New Florence

Secluded 2 bedroom home close to Hermann
9.8 out of 10, Exceptional, (46)
"We thoroughly enjoyed our stay! The house was very clean and spacious for our group of 6. Very happy with our experience!"
United States
Renee R.
$237 nightly
The price is $250
Jan 5 - Jan 6
Total with taxes and fees
Secluded 2 bedroom home close to Hermann
Interior
Wine Alley West Suite

Apartment in Hermann

Wine Alley West Suite
9.0 out of 10, Wonderful, (47)
"The VRBO was clean and very warming! We had a great time! "
United States
Amy R.
Wine Alley West Suite
House (3 Bedrooms) | Interior
Downtown Hermann Vacation Home Near Wineries!

Cottage in Hermann

Downtown Hermann Vacation Home Near Wineries!
3.0 star property
10.0 out of 10, Exceptional, (1)
"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
Jan 5 - Jan 6
Total with taxes and fees
Downtown Hermann Vacation Home Near Wineries!
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Riverview Cottage. 5 minute walk to downtown

Vacation Home in Hermann

Cozy Riverview Cottage. 5 minute walk to downtown
9.8 out of 10, Exceptional, (43)
"Wonderful stay at the cutest little cottage in Herrmann! "
United States
Tami L.
$178 nightly
The price is $196
Jan 6 - Jan 7
Total with taxes and fees
Cozy Riverview Cottage. 5 minute walk to downtown
Exterior detail
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

Aparthotel in McKittrick

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
10.0 out of 10, Exceptional, (2)
"Loved this placed, would definitely come back!"
United States
Cody W.
$258 nightly
The price is $286
Jan 6 - Jan 7
Total with taxes and fees
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
Fridge, microwave, oven, stovetop
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

Aparthotel in Hermann

Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
$258 nightly
The price is $286
Jan 6 - Jan 7
Total with taxes and fees
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Exterior detail
Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann

Aparthotel in Hermann

Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann
8.8 out of 10, Excellent, (8)
"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.
$258 nightly
The price is $286
Jan 6 - Jan 7
Total with taxes and fees
Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann
Outdoor dining
Ash Creek Guesthouse - Downtown Historic Hermann

Vacation Home in Hermann

Ash Creek Guesthouse - Downtown Historic Hermann
9.8 out of 10, Exceptional, (46)
"Great!!"
United States
Robert S.
$333 nightly
The price is $377
Jan 5 - Jan 6
Total with taxes and fees
Ash Creek Guesthouse - Downtown Historic Hermann
Exterior detail
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

Apartment in Hermann

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
10.0 out of 10, Exceptional, (4)
"So pretty and perfect for our weekend."
United States
Katherine B.
$258 nightly
The price is $286
Jan 6 - Jan 7
Total with taxes and fees
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Terrace/patio
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!

Vacation Home in Hermann

Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
10.0 out of 10, Exceptional, (19)
"Lovely place to stay. In fact we spent most of the weekend at the house just chilling and hanging out. Would definitely stay again. Host was very nice and responded quickly with any questions we had. "
United States
Tracy B.
$282 nightly
The price is $318
Jan 6 - Jan 7
Total with taxes and fees
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
Fridge, microwave, oven, stovetop
Hillside Cottage in Beautiful Downtown Hermann

Vacation Home in Hermann

Hillside Cottage in Beautiful Downtown Hermann
9.2 out of 10, Wonderful, (25)
"Check-in easy and kitchen was good"
United States
Stewart H.
$325 nightly
The price is $369
Jan 5 - Jan 6
Total with taxes and fees
Hillside Cottage in Beautiful 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

Hermann Crown Suites

Hermann Crown Suites

10/10 Excellent
"Fabulous old hotel, great location, staff were wonderful, would absolutely stay again in a heartbeat."
Kathleen 1-night trip
Posted 3 days ago
Hermann Crown Suites

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 $196 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?

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 Daniel Boone Conservation Area 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.