Holiday Rentals in Montgomery City

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Our top choices for Montgomery City holiday rentals

9.4 out of 10, Exceptional, (6 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.
The price is €313
includes taxes & fees
16 Jan - 17 Jan
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

Holiday Home in Berger

Archie’s House
10.0 out of 10, Exceptional, (36 reviews)
"Everything was very nice!!! I highly recommend. "
United States
Mary T.
The price is €360
includes taxes & fees
16 Jan - 17 Jan
Archie’s House
10.0 out of 10, Exceptional, (114 reviews)
"Nice property, with great view of Hermann"
United States
Mike L.
The price is €148
includes taxes & fees
10 Feb - 11 Feb
Gipfel Suite - Himmel Haus Bed & Breakfast
10.0 out of 10, Exceptional, (56 reviews)
"Very nice suite. Excellent location. Host was very friendly!"
United States
Eric R.
The price is €180
includes taxes & fees
18 Jan - 19 Jan
The Monet Suite is one of our four rooms.

Apartment in Hermann

Nature`s Nook by Zia, Hermann
10.0 out of 10, Exceptional, (4 reviews)
"This room was so relaxing. Our host was the sweetest. Very attentive. They have gone above and beyond thinking of all the details to make your stay comfortable.We will definitely return again. "
United States
Shelly V.
The price is €237
includes taxes & fees
12 Feb - 13 Feb
Nature`s Nook by Zia, Hermann
4.5 star property
9.8 out of 10, Exceptional, (28 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
The price is €208
includes taxes & fees
19 Jan - 20 Jan
The Mercantile on the Katy Trail
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.
The price is €163
includes taxes & fees
22 Jan - 23 Jan
Plenty room for relaxing and downtown location to walk around!
9.8 out of 10, Exceptional, (45 reviews)
"Wonderful stay at the cutest little cottage in Herrmann! "
United States
Tami L.
The price is €234
includes taxes & fees
20 Jan - 21 Jan
Cozy Riverview Cottage. 5 minute walk to downtown
10.0 out of 10, Exceptional, (4 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is €234
includes taxes & fees
18 Jan - 19 Jan
Charming 2-bedroom house in fabulous downtown Hermann
3.0 star property
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
The price is €590
includes taxes & fees
13 Feb - 14 Feb
Downtown Hermann Vacation Home Near Wineries!
9.4 out of 10, Exceptional, (52 reviews)
"Convenient location and clean rooms. Beds were very uncomfortable."
United States
Brady S.
The price is €221
includes taxes & fees
18 Jan - 19 Jan
Ash Creek Suite - In Downtown Historic Hermann

Holiday Home in New Florence

Secluded 2 bedroom home close to Hermann
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
The price is €222
includes taxes & fees
21 Jan - 22 Jan
Secluded 2 bedroom home close to Hermann
10.0 out of 10, Exceptional, (2 reviews)
"Loved this placed, would definitely come back!"
United States
Cody W.
The price is €249
includes taxes & fees
20 Jan - 21 Jan
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
The price is €249
includes taxes & fees
20 Jan - 21 Jan
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
9.8 out of 10, Exceptional, (47 reviews)
"Great!!"
United States
Robert S.
The price is €331
includes taxes & fees
18 Jan - 19 Jan
Ash Creek Guesthouse - Downtown Historic Hermann
9.6 out of 10, Exceptional, (25 reviews)
"Great location, easy walking distance to downtown! "
United States
Cheryl M.
The price is €331
includes taxes & fees
18 Jan - 19 Jan
Kork Haus - Whole house rental in Downtown Hermann
10.0 out of 10, Exceptional, (4 reviews)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is €249
includes taxes & fees
20 Jan - 21 Jan
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
9.2 out of 10, Wonderful, (25 reviews)
"Check-in easy and kitchen was good"
United States
Stewart H.
The price is €331
includes taxes & fees
18 Jan - 19 Jan
Hillside Cottage in Beautiful Downtown Hermann
9.8 out of 10, Exceptional, (53 reviews)
"Great location, cool place"
United States
Dave J.
The price is €180
includes taxes & fees
18 Jan - 19 Jan
The Da Vinci Suite is one of our four rooms.
10.0 out of 10, Exceptional, (20 reviews)
"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.
The price is €282
includes taxes & fees
20 Jan - 21 Jan
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montgomery City holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery City holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery City holiday rentals we have selected for you start as low as €183 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montgomery City rentals

At Expedia, we put the best Montgomery City holiday 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 holiday.

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 holiday rental in Montgomery City?

Yes, there are holiday rentals close to the most popular sights in Montgomery City, or you can select a more secluded option if you're looking for a relaxing stay. Montgomery City is known for its parks.

What are some of the best holiday rentals that Montgomery City has to offer?

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!: This holiday home rental outside of Montgomery City is located in the city centre, and has a garden, a BBQ 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 that 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 wider area.

What’s a holiday rental in Montgomery City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery City. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.