Holiday Homes in Montgomery City

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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

Featured Holiday Homes in Montgomery City

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, (46)
"This is a nice place to stay. It is right there by downtown and provides walking access to many shops, breweries and distilleries.It was clean and comfortable. We only had a couple of hiccups but they were resolved. Be sure to check out the book with instructions for the heat. We were there on a cold weekend and were confused at how to operate the heat as it was marked a/c only. We did have an issue which the owners dealt with and we appreciated that so much!We would stay here again. Only...
Historic District Inn 4 Bed/ 3 Bath in the heart of 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, (20)
"Such a cute little cottage right on the edge of town! Beautiful view!!! Easy walkability to shops on Main Street! "
The price is AU$468
includes taxes & fees
1 Mar - 2 Mar
Cozy Riverview Cottage. 5 minute walk to downtown
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, (90)
"The pictures do not do this house justice! It has so much more charm to offer, this will be our go to for every Hermann visit. "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Frene Valley Guest House
Fridge, microwave, oven, stovetop

Frene Valley Guest House

10.0 out of 10, Exceptional, (79)
"The property is fairly new. Must have bean a tear down. VERY CLEAN! All four bedrooms upstairs and 3 full baths and one half bath. Perfect for the four of us. Really comfortable beds. Three couches by the TV made it great to visit in the evenings. Great location to shops and restaurants. Our original plan was to use the trolley to visit wineries, but we ended up shopping all day! Would highly recommend!"
Frene Valley Guest House
Brick Bungalow
Fridge, microwave, oven, stovetop

Brick Bungalow

10.0 out of 10, Exceptional, (47)
"Perfect location. 1.8 miles and an easy drive to Hermann Hills wedding venue. About one black from the main street of and therefore close to everything in town. Home was very clean. Comfortable beds. Plenty of towels and basic supplies. Exceptional communicaton and support from owner and property manager. Would stay again. Highly recommended. "
Brick Bungalow
Gipfel Suite - Himmel Haus Bed & Breakfast
Outdoor dining

Gipfel Suite - Himmel Haus Bed & Breakfast

10.0 out of 10, Exceptional, (85)
"Cute, clean room with private outside door access provided additional privacy for our visit. We enjoyed the breakfast and owner was quick to answer questions. "
The price is AU$269
includes taxes & fees
4 Mar - 5 Mar
Gipfel Suite - Himmel Haus Bed & Breakfast
Modern Victorian - 1910 Guesthaus
Exterior

Modern Victorian - 1910 Guesthaus

10.0 out of 10, Exceptional, (26)
"The house is very clean and the beds are comfy!"
Modern Victorian - 1910 Guesthaus
Ash Creek Suite - In Downtown Historic Hermann
Dining

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (44)
"Walking distance from main area"
The price is AU$460
includes taxes & fees
3 Mar - 4 Mar
Ash Creek Suite - In Downtown Historic Hermann
Suite on Schiller
Fridge, microwave, oven, coffee/tea maker

Suite on Schiller

9.8 out of 10, Exceptional, (98)
"We thoroughly enjoyed our stay here. There are lots of great venues within walking distance of this property. "
Suite on Schiller
The Artists Suites, Jackson Pollock Suite
Interior

The Artists Suites, Jackson Pollock Suite

9.8 out of 10, Exceptional, (43)
"Hosts were very responsive and helpful. Great place to stay. We got a little confused on how to enter the property, but we figured it out! Comfortable and warm!"
The price is AU$253
includes taxes & fees
2 Mar - 3 Mar
The Artists Suites, Jackson Pollock Suite
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, (25)
"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!!!
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, (45)
"The only complaint was that we had no soap or shampoo. The host did fix the issue though. House is very clean. Area was very nice."
Suite #4 - Adorable 2 Bed Suite in Downtown Hermann
Downtown Location, Door to Door Private Shuttle, Great View, & Free Breakfasts
Bar (on property)

Downtown Location, Door to Door Private Shuttle, Great View, & Free Breakfasts

9.6 out of 10, Exceptional, (81)
"House was clean. A little dated. If you are arriving in bike while riding the Katy, it is a tough climb on the hilly streets. Great views. "
The price is AU$464
includes taxes & fees
28 Feb - 1 Mar
Downtown Location, Door to Door Private Shuttle, Great View, & Free Breakfasts
Brick Cellar Estate
Exterior

Brick Cellar Estate

2.0 star property
Brick Cellar Estate
The House on Wine Alley
Interior

The House on Wine Alley

9.0 out of 10, Wonderful, (40)
"We loved the place and proximity to town"
The price is AU$509
includes taxes & fees
2 Mar - 3 Mar
The House on Wine Alley
Suite #3 - 2 Bed 1 Bath Suite at Suites on 3rd
Interior

Suite #3 - 2 Bed 1 Bath Suite at Suites on 3rd

9.8 out of 10, Exceptional, (59)
"Loved this suite!! It was perfect and cozy. Close to everything in town. The owner was wonderful and very responsive and sweet. Highly recommend!!!! "
Suite #3 - 2 Bed 1 Bath Suite at Suites on 3rd
The Artists Suites, Claude Monet Suite
Interior

The Artists Suites, Claude Monet Suite

10.0 out of 10, Exceptional, (34)
"The room was beautifully decorated and the little perks were great! A few snacks were provided along with waters and enough towels and toiletries. Very clean, very quiet and very enjoyable. You won’t regret staying here! "
The price is AU$277
includes taxes & fees
2 Mar - 3 Mar
The Artists Suites, Claude Monet Suite
Secluded 2 bedroom home close to Hermann
Outdoor dining

Secluded 2 bedroom home close to Hermann

9.8 out of 10, Exceptional, (37)
"We only had a short stay, but it was very nice. Such a cute, secluded place right outside of Herman. Worked out perfect for our winery tour. "
The price is AU$437
includes taxes & fees
2 Mar - 3 Mar
Secluded 2 bedroom home close to Hermann
Archie’s House
3 bedrooms, iron/ironing board, WiFi, bed sheets

Archie’s House

10.0 out of 10, Exceptional, (28)
"The house was clean and was an amazing stay for wanting to get to Hermann to go to the wineries "
The price is AU$657
includes taxes & fees
28 Feb - 1 Mar
Archie’s House
Two-House Private Country Retreat - 4 Bedrooms and 3.5 Baths
Exterior

Two-House Private Country Retreat - 4 Bedrooms and 3.5 Baths

10.0 out of 10, Exceptional, (23)
"Cannot say enough good about this property and property owner! The attention to detail is second-to-none ... and if I started a list (beautiful decor, cozy fireplaces, magnificent farmhouse table and chef-ready kitchens) I'd surely miss important details (Alexa, multiple coffee stations, Ghirardelli chocolates). This was ... by far ... the best vrbo we've ever encountered."
Two-House Private Country Retreat - 4 Bedrooms and 3.5 Baths
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

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, (90)
"The pictures do not do this house justice! It has so much more charm to offer, this will be our go to for every Hermann visit. "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
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, (155)
"We had a great stay! Cute house, clean, plenty of space and great location. Most places downtown were in walking distance. We will definitely be back!"
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
The House on Wine Alley
Interior

The House on Wine Alley

9.0 out of 10, Wonderful, (40)
"We loved the place and proximity to town"
The price is AU$509
includes taxes & fees
2 Mar - 3 Mar
The House on Wine Alley
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.