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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 73 Vacation Homes in Montgomery City with updated reviews, rates, and availability.

The House on Wine Alley
Interior

The House on Wine Alley

9.0 out of 10, Wonderful, (40)
"Great place to stay in the heart of Hermann! Definitely recommend!"
The price is AED 845
AED 1,178 total
includes taxes & fees
11 May - 12 May
The House on Wine Alley
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, (25)
"Such a cute little cottage right on the edge of town! Beautiful view!!! Easy walkability to shops on Main Street! "
The price is AED 735
AED 1,072 total
includes taxes & fees
12 May - 13 May
Cozy Riverview Cottage. 5 minute walk to downtown
Magnolia Inn
Fridge, microwave, oven, stovetop

Magnolia Inn

9.8 out of 10, Exceptional, (34)
"Perfect place to stay in Hermann!"
Magnolia Inn
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Exterior

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

9.8 out of 10, Exceptional, (50)
"The house was awesome, very spacious. We had a great time!"
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
TV

Suite #4 - Adorable 2 Bed Suite in Downtown Hermann

9.8 out of 10, Exceptional, (47)
"Excellent location, very cute place. I would stay again. Perfect for walking to so many places there. "
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
Gipfel Suite - Himmel Haus Bed & Breakfast
Outdoor dining

Gipfel Suite - Himmel Haus Bed & Breakfast

10.0 out of 10, Exceptional, (89)
"Very nice clean room and great breakfast. Quiet neighborhood."
The price is AED 364
AED 616 total
includes taxes & fees
21 May - 22 May
Gipfel Suite - Himmel Haus Bed & Breakfast
Eduard Haus in the Downtown Historic District of Hermann, Missouri
Outdoor dining

Eduard Haus in the Downtown Historic District of Hermann, Missouri

8.0 out of 10, Very Good, (1)
"We had a great time! The house is located in walking distance of all restaurants and bars. It was clean and we couldn’t get the AC to work and the owners were very quick to respond and help fix it. We loved how many beds there was. The only complaint is how hard the beds and pillows are. Had a great time!"
Eduard Haus in the Downtown Historic District of Hermann, Missouri
Ash Creek Suite - In Downtown Historic Hermann
Dining

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (46)
"Such a great place to stay! "
The price is AED 735
AED 1,271 total
includes taxes & fees
11 May - 12 May
Ash Creek Suite - In Downtown Historic 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, (35)
"We loved the home. It was a great location and a beautiful property. The showers had great pressure!"
The price is AED 1,102
AED 2,116 total
includes taxes & fees
11 May - 12 May
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
The Laughing Boar, perfectly located downtown
Exterior

The Laughing Boar, perfectly located downtown

10.0 out of 10, Exceptional, (44)
"We had a great stay at the Boar House. House was lovely as described. Easy walking distance to many activities. Would stay at again. "
The price is AED 1,469
AED 2,586 total
includes taxes & fees
11 May - 12 May
The Laughing Boar, perfectly located downtown
Brick Bungalow
Fridge, microwave, oven, stovetop

Brick Bungalow

10.0 out of 10, Exceptional, (49)
"We came to Hermann to enjoy the Oktoberfest and to celebrate my husband turning 65. Weather was fantastic and the Brick Bungalow was a perfect & convenient spot for home base!"
Brick Bungalow
Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
Interior

Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!

10.0 out of 10, Exceptional, (30)
"Beautifully kept property, comfortable, and with character. We would happily stay again!"
Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
A Charming Home newly remodeled and furnished
Smart TV

A Charming Home newly remodeled and furnished

10.0 out of 10, Exceptional, (62)
"This was probably the nicest Vrbo I,ve stayed in. Will definitely stay here again. "
A Charming Home newly remodeled and furnished
Private Bathroom, Private Entrance, The Cobbler Suite is perfect for your weekend getaway! Park the car and walk to shops, restaurants, wineries, distilleries, breweries, tasting rooms and more!
Fridge, microwave, coffee/tea maker

Private Bathroom, Private Entrance, The Cobbler Suite is perfect for your weekend getaway! Park the car and walk to shops, restaurants, wineries, distilleries, breweries, tasting rooms and more!

10.0 out of 10, Exceptional, (34)
"Cozy room, clean and great location within and easy walk to all the main attractions."
The price is AED 579
AED 747 total
includes taxes & fees
10 May - 11 May
Private Bathroom, Private Entrance, The Cobbler Suite is perfect for your weekend getaway! Park the car and walk to shops, restaurants, wineries, distilleries, breweries, tasting rooms and more!
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Interior

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (95)
"Enjoyed the quietness of this immaculate home! Loved the cellar! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
The Artists Suites, Jackson Pollock Suite
Interior

The Artists Suites, Jackson Pollock Suite

9.8 out of 10, Exceptional, (45)
"Great place to stay , center of town , everything is within walking distance , everything was simple , and made easy for the guests"
The price is AED 364
AED 580 total
includes taxes & fees
11 May - 12 May
The Artists Suites, Jackson Pollock Suite
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
Fridge, microwave, oven, stovetop

The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

10.0 out of 10, Exceptional, (158)
"It was a great weekend in a cozy cottage "
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
The Farmhouse Inn: 3 bed, 3.5 whole house rental
Fridge, microwave, oven, stovetop

The Farmhouse Inn: 3 bed, 3.5 whole house rental

10.0 out of 10, Exceptional, (101)
"Had a great stay and loved this house! So clean, exactly as pictured, great to come back to after a long day and be able to relax with friend"
The Farmhouse Inn: 3 bed, 3.5 whole house rental
Newly remodeled home in Historic Hermann Wine Counrtry.
Exterior

Newly remodeled home in Historic Hermann Wine Counrtry.

10.0 out of 10, Exceptional, (67)
"The property was amazing and so clean! Jessica was great to work with and answered all questions. A short ride to all the wineries and downtown. "
The price is AED 1,653
AED 3,075 total
includes taxes & fees
11 May - 12 May
Newly remodeled home in Historic Hermann Wine Counrtry.
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, (51)
"We had a nice weekend at this nice place. "
The price is AED 1,102
AED 1,392 total
includes taxes & fees
11 May - 12 May
Your home away from home! The Branson Country B&B in Hermann,Mo
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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Other property types in Montgomery City

Glamping with gorgeous sunset views, trolley to all wineries
Fridge, microwave, oven, stovetop

Glamping with gorgeous sunset views, trolley to all wineries

10.0 out of 10, Exceptional, (2)
"It was a wonderful stay for 5 of us girls going to Herman for a day at the Winery. This location was perfect, just 7 minutes up the road from Downtown Herman. The trolley picked us up with no issue. Very quiet location, perfect for a quick getaway!"
The price is AED 551
AED 845 total
includes taxes & fees
11 May - 12 May
Glamping with gorgeous sunset views, trolley to all wineries
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Interior

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (95)
"Enjoyed the quietness of this immaculate home! Loved the cellar! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
TV

Suite #4 - Adorable 2 Bed Suite in Downtown Hermann

9.8 out of 10, Exceptional, (47)
"Excellent location, very cute place. I would stay again. Perfect for walking to so many places there. "
Suite #4 - Adorable 2 Bed Suite in 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.