Search Vacation Homes in Montgomery City

Start date: Check-in selected.
End date: Check-out
    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

Next weekend
19 Sep - 21 Sep
In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Vacation Homes in Montgomery City

Our top choices for Montgomery City vacation homes

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

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

8.0 out of 10, Very Good, (2)
"No wi-fi. Mediocre property undergoing some renovations. Way over-priced for a 2 bedroom. (The 3rd bedroom had a bunk bed with 2 top bunks). The living room couches were very hard and uncomfortable. The patio area was broken up and weedy. The Owners would benefit from adding a pool table in the basement, a patio area with a gas grill, patio furniture, hot tub &/or pool. The deck was nice but it wasn’t on the sunny side of the house. "
The price is SAR 760
SAR 1,334 total
includes taxes & fees
13 Sep - 14 Sep
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
NEW! Villa Bella Elegant Hermann Farmhouse with Wine Bar, Fire Pit &Trolley Ride
Interior

NEW! Villa Bella Elegant Hermann Farmhouse with Wine Bar, Fire Pit &Trolley Ride

10.0 out of 10, Exceptional, (6)
"We had an amazing (much needed) holiday away together in the most beautiful and cozy Villa Bella house! Lots to do in the area and the host was so helpful and made sure we had everything we needed. 10/10 we will be back! "
The price is SAR 478
SAR 1,218 total
includes taxes & fees
15 Sep - 16 Sep
NEW! Villa Bella Elegant Hermann Farmhouse with Wine Bar, Fire Pit &Trolley Ride
Quiet, country experience - 5 miles from Hermann.
Interior

Quiet, country experience - 5 miles from Hermann.

Quiet, country experience - 5 miles from Hermann.
The Da Vinci Suite is one of our four rooms.
Interior

The Da Vinci Suite is one of our four rooms.

9.8 out of 10, Exceptional, (48)
"Great place and location, very clean."
The price is SAR 409
SAR 715 total
includes taxes & fees
14 Sep - 15 Sep
The Da Vinci Suite is one of our four rooms.
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Exterior detail

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

10.0 out of 10, Exceptional, (3)
"This was the perfect place for a girls weekend! it was a little concerning getting there as it is down a narrow path that appears very low income. However the property feels very secure and safe! The room was very clean and updated, it had everything we needed and more. The open atmosphere made it feel even larger than expected. The large sitting space allowed for a cozy lounge area that we very much enjoyed. The location backing up to the MKT trail was so wonderful for morning and evening...
The price is SAR 806
SAR 1,006 total
includes taxes & fees
23 Sep - 24 Sep
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Ash Creek Suite - In Downtown Historic Hermann
Dining

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (49)
"This little house was so cute and the perfect size for 2 couples. Great location! We will definitely stay here again. "
The price is SAR 469
SAR 935 total
includes taxes & fees
14 Sep - 15 Sep
Ash Creek Suite - In Downtown Historic Hermann
Charming 2-bedroom house in fabulous downtown Hermann
Exterior

Charming 2-bedroom house in fabulous downtown Hermann

The price is SAR 469
SAR 993 total
includes taxes & fees
14 Sep - 15 Sep
Charming 2-bedroom house in fabulous downtown Hermann
Cozy Riverview Cottage. 5 minute walk to downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (32)
"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 SAR 675
SAR 998 total
includes taxes & fees
14 Sep - 15 Sep
Cozy Riverview Cottage. 5 minute walk to downtown
Gipfel Suite - Himmel Haus Bed & Breakfast
Outdoor dining

Gipfel Suite - Himmel Haus Bed & Breakfast

10.0 out of 10, Exceptional, (107)
"Very clean and nice. Wonderful breakfast. Would definitely stay here again."
The price is SAR 371
SAR 629 total
includes taxes & fees
15 Sep - 16 Sep
Gipfel Suite - Himmel Haus Bed & Breakfast
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Fridge, microwave, oven, stovetop

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

The price is SAR 806
SAR 991 total
includes taxes & fees
7 Oct - 8 Oct
Vaudeville Suite, Romantic King Stay Just 4 Min from Hermann Wineries
Newly Renovated "Wine Cork Escape"!
Fridge, microwave, oven, stovetop

Newly Renovated "Wine Cork Escape"!

10.0 out of 10, Exceptional, (39)
"Our repeat stay was as just as great as the first. Beds are comfy and the location is quiet. We will definitely book when we are in the area again."
Newly Renovated "Wine Cork Escape"!
Spacious House walking distance from downtown Hermann
Property grounds

Spacious House walking distance from downtown Hermann

10.0 out of 10, Exceptional, (14)
"We’ve stayed at the house a couple years now & always enjoy it. The host is always very accommodating. "
The price is SAR 1,013
SAR 2,025 total
includes taxes & fees
15 Sep - 16 Sep
Spacious House walking distance from downtown Hermann
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
Terrace/patio

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

10.0 out of 10, Exceptional, (13)
"We were in town for a family wedding and this was the perfect house and location. A hidden gem with so many ammenities, exactly what we needed."
The price is SAR 930
SAR 1,200 total
includes taxes & fees
16 Sep - 17 Sep
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
Kork Haus - Whole house rental in Downtown Hermann
Terrace/patio

Kork Haus - Whole house rental in Downtown Hermann

9.6 out of 10, Exceptional, (22)
"Absolutely great stay at the Kork Haus!"
The price is SAR 882
SAR 1,528 total
includes taxes & fees
14 Sep - 15 Sep
Kork Haus - Whole house rental in Downtown Hermann
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
Dining

Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

10.0 out of 10, Exceptional, (45)
"Great place to stay"
The price is SAR 1,013
SAR 2,006 total
includes taxes & fees
14 Sep - 15 Sep
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
The House on Wine Alley
Interior

The House on Wine Alley

9.0 out of 10, Wonderful, (49)
"Lovely house with anything we could need! Totally enjoyed our stay! Thank you!"
The price is SAR 863
SAR 1,192 total
includes taxes & fees
14 Sep - 15 Sep
The House on Wine Alley
Your home away from home! The Branson Country B&B in Hermann,Mo
Outdoor dining

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

9.8 out of 10, Exceptional, (57)
"Certainly enjoyed our stay at Branson Country B&B. Had everything we needed. House was very clean and comfortable. Wish we could have stayed longer. Would definitely recommend Kelly and her B&B."
The price is SAR 1,126
SAR 1,407 total
includes taxes & fees
15 Sep - 16 Sep
Your home away from home! The Branson Country B&B in Hermann,Mo
Ash Creek Guesthouse - Downtown Historic Hermann
Outdoor dining

Ash Creek Guesthouse - Downtown Historic Hermann

9.8 out of 10, Exceptional, (46)
"This house was very nice, everything was as described, online pictures are accurate. The location was perfect for enjoying the festivities."
The price is SAR 882
SAR 1,528 total
includes taxes & fees
14 Sep - 15 Sep
Ash Creek Guesthouse - Downtown Historic Hermann
Secluded 2 bedroom home close to Hermann
Outdoor dining

Secluded 2 bedroom home close to Hermann

9.8 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay! The house was very clean and spacious for our group of 6. Very happy with our experience!"
The price is SAR 675
SAR 936 total
includes taxes & fees
14 Sep - 15 Sep
Secluded 2 bedroom home close to 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.
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
"The grounds and the building itself were clean, and well maintained. Breakfast was plentiful and good. Beds are comfortable also. Location was not far from the interstate, and near to shopping nearby. Overall, a good experience and would stay here again in the future."
Kevin 1-night trip
Posted 4 days ago
Best Western Teal Lake Inn