Montgomery City Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

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

9.2 out of 10, Wonderful, (5)
"We enjoyed our time in Hermann and this home gave us a welcome space to relax and unwind after visiting the local wineries. IT is a bit off the beaten path, but well worth the short drive. The host was responsive and gracious.Thanks for a great stay!"
United States
Kathy B.
The price is ￥31,547
￥55,411 total
includes taxes & fees
Dec 11 - Dec 12
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Dining
Archie’s House

Vacation Home in Berger

10.0 out of 10, Exceptional, (36)
"Everything was very nice!!! I highly recommend. "
United States
Mary T.
The price is ￥46,402
￥63,850 total
includes taxes & fees
Dec 23 - Dec 24
Archie’s House
Outdoor dining
Gipfel Suite - Himmel Haus Bed & Breakfast

Vacation Home in Hermann

10.0 out of 10, Exceptional, (113)
"Very cute room. Perfect for an overnight stay!"
United States
Angel H.
The price is ￥15,423
￥26,121 total
includes taxes & fees
Dec 15 - Dec 16
Gipfel Suite - Himmel Haus Bed & Breakfast
Front of property
The Mercantile on the Katy Trail

Aparthotel in Hermann

4.5 star property
9.8 out of 10, Exceptional, (28)
"Great place, fully stocked and clean!"
United States
Lauren
The price is ￥35,158
￥37,786 total
includes taxes & fees
Dec 11 - Dec 12
The Mercantile on the Katy Trail
Interior
The Da Vinci Suite is one of our four rooms.

Aparthotel in Hermann

9.8 out of 10, Exceptional, (52)
"Great place and location, very clean."
United States
Scott B.
The price is ￥18,508
￥32,027 total
includes taxes & fees
Dec 15 - Dec 16
The Da Vinci Suite is one of our four rooms.
Dining
Nature`s Nook by Zia, Hermann

Apartment in 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
The price is ￥27,263
￥41,837 total
includes taxes & fees
Dec 18 - Dec 19
Nature`s Nook by Zia, Hermann
House (3 Bedrooms) | Interior
Downtown Hermann Vacation Home Near Wineries!

Cottage in Hermann

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
The price is ￥75,247
￥107,240 total
includes taxes & fees
Dec 11 - Dec 12
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

9.8 out of 10, Exceptional, (43)
"Super cute!"
United States
Meghan W.
The price is ￥19,069
￥29,931 total
includes taxes & fees
Dec 16 - Dec 17
Cozy Riverview Cottage. 5 minute walk to downtown
Dining
Ash Creek Suite - In Downtown Historic Hermann

Vacation Home in Hermann

9.4 out of 10, Exceptional, (51)
"Met our needs"
United States
Craig C.
The price is ￥19,474
￥39,292 total
includes taxes & fees
Dec 15 - Dec 16
Ash Creek Suite - In Downtown Historic Hermann
Exterior detail
Plenty room for relaxing and downtown location to walk around!

Apartment in Hermann

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.
The price is ￥22,395
￥28,867 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Plenty room for relaxing and downtown location to walk around!
Outdoor dining
Secluded 2 bedroom home close to Hermann

Vacation Home in New Florence

9.8 out of 10, Exceptional, (45)
"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.
The price is ￥28,042
￥38,879 total
includes taxes & fees
Dec 11 - Dec 12
Secluded 2 bedroom home close to Hermann
Exterior
Charming 2-bedroom house in fabulous downtown Hermann

Vacation Home in Hermann

10.0 out of 10, Exceptional, (3)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥19,474
￥41,392 total
includes taxes & fees
Dec 14 - Dec 15
Charming 2-bedroom house in fabulous downtown Hermann
Interior
Wine Alley West Suite

Apartment in Hermann

9.0 out of 10, Wonderful, (47)
"We enjoyed our stay very much. Nice apartment with everything we needed. Thanks "
United States
LeeAnn J.
The price is ￥22,590
￥32,989 total
includes taxes & fees
Dec 11 - Dec 12
Wine Alley West Suite
Fridge, microwave, oven, stovetop
Wine Alley East suite

Apartment in Hermann

9.4 out of 10, Exceptional, (77)
"Great location clean safe "
United States
Toshmon
The price is ￥22,590
￥32,989 total
includes taxes & fees
Dec 11 - Dec 12
Wine Alley East suite
Fridge, microwave, oven, stovetop
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries

Aparthotel in Hermann

The price is ￥35,333
￥44,169 total
includes taxes & fees
Dec 23 - Dec 24
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Exterior detail
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

Aparthotel in McKittrick

10.0 out of 10, Exceptional, (2)
"Loved this placed, would definitely come back!"
United States
Cody W.
The price is ￥35,333
￥44,169 total
includes taxes & fees
Dec 16 - Dec 17
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
Exterior detail
Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann

Aparthotel in 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.
The price is ￥35,333
￥44,169 total
includes taxes & fees
Dec 16 - Dec 17
Katy Suite - Chic 2BR Stay on Katy Trail in Historic Mercantile near Hermann
Exterior detail
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

Apartment in Hermann

10.0 out of 10, Exceptional, (4)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is ￥35,333
￥44,793 total
includes taxes & fees
Dec 23 - Dec 24
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Interior
The House on Wine Alley

Vacation Home in Hermann

9.0 out of 10, Wonderful, (54)
"Great location. Fun town. "
United States
sandy g.
The price is ￥35,832
￥49,484 total
includes taxes & fees
Dec 11 - Dec 12
The House on Wine Alley
Outdoor dining
Ash Creek Guesthouse - Downtown Historic Hermann

Vacation Home in Hermann

9.8 out of 10, Exceptional, (46)
"Great!!"
United States
Robert S.
The price is ￥31,158
￥56,812 total
includes taxes & fees
Dec 21 - Dec 22
Ash Creek Guesthouse - 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

Quality Inn

Quality Inn

10/10 Excellent
"Clean areas"
Errol 1-night trip
Posted 2 days ago
Quality Inn

Find out more about Montgomery City

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Look no further and take a look at our great range of rental properties in Montgomery City!

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 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.