Montgomery City Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Montgomery City vacation rentals

Smart TV

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

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Hermann
9.8 out of 10, Exceptional, (11 reviews)
"Great place to ring in the New Year under clear skies where you could see all the stars "
United States
Nicholas N.
The price is ￥31,914
￥57,623 total
includes taxes & fees
May 17 - May 18
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Fridge, microwave, oven, stovetop

Glamping with gorgeous sunset views, trolley to all wineries

Glamping with gorgeous sunset views, trolley to all wineries
Berger
9.6 out of 10, Exceptional, (10 reviews)
"Nice place to stay, super clean and cute! "
United States
Amanda E.
The price is ￥23,579
￥33,391 total
includes taxes & fees
May 26 - May 27
Glamping with gorgeous sunset views, trolley to all wineries
3 bedrooms, iron/ironing board, WiFi, bed sheets

Archie’s House

Archie’s House
Berger
10.0 out of 10, Exceptional, (36 reviews)
"Cutest house! Very well kept and clean! Exceeded expectations and would definitely stay again if we were ever in the area! Thanks for a great stay! "
United States
Jennifer S.
The price is ￥61,281
￥81,716 total
includes taxes & fees
May 26 - May 27
Archie’s House
Exterior

Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (1 review)
"This place was seriously a slice of heaven. The hosts were very attentive and welcoming! The house was fully stocked with anything we may have needed, we will definitely be back!"
United States
Kylee F.
The price is ￥19,020
￥32,980 total
includes taxes & fees
May 21 - May 22
Papa's Cabin - 40 acres & 5 acre lake!
Comfort Loft, 2 Queen Beds, Bathtub, Garden View | Living area | 45-inch Smart TV with digital channels, books, streaming services

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (30 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
The price is ￥31,901
￥34,286 total
includes taxes & fees
May 19 - May 20
The Mercantile on the Katy Trail
Property grounds

Nature`s Nook by Zia, Hermann

Nature`s Nook by Zia, Hermann
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"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 ￥27,508
￥42,213 total
includes taxes & fees
May 26 - May 27
Nature`s Nook by Zia, Hermann
Smart TV, DVD player

Cozy Riverview Cottage. 5 minute walk to downtown

Cozy Riverview Cottage. 5 minute walk to downtown
Hermann
9.8 out of 10, Exceptional, (49 reviews)
"This cottage was super cute and nice to stay at. We really enjoyed our stay. "
United States
Alisha Q.
The price is ￥28,368
￥41,126 total
includes taxes & fees
May 14 - May 15
Cozy Riverview Cottage. 5 minute walk to downtown
Outdoor dining

Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
The price is ￥28,368
￥39,668 total
includes taxes & fees
May 14 - May 15
Secluded 2 bedroom home close to Hermann
Interior

Germantown Inn & Lounge

Germantown Inn & Lounge
Hermann
The price is ￥19,885
￥26,008 total
includes taxes & fees
May 26 - May 27
Germantown Inn & Lounge
Outdoor dining

Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast
Hermann
10.0 out of 10, Exceptional, (122 reviews)
"Renee was an excellent host. The hot morning breakfasts were delicious. The property was quiet and just a short walk from downtown Hermann."
United States
Dala
The price is ￥15,562
￥25,445 total
includes taxes & fees
May 26 - May 27
Gipfel Suite - Himmel Haus Bed & Breakfast
Outdoor dining

Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann
Hermann
9.4 out of 10, Exceptional, (52 reviews)
"Great area, close to everything. House was perfect"
United States
ELIZABETH K.
The price is ￥25,150
￥46,754 total
includes taxes & fees
May 21 - May 22
Ash Creek Suite - In Downtown Historic Hermann
Exterior

Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.8 out of 10, Exceptional, (9 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is ￥23,640
￥46,877 total
includes taxes & fees
May 14 - May 15
Charming 2-bedroom house in fabulous downtown Hermann
Interior

Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (51 reviews)
"Close to everything downtown. Reasonable price. We were gone most of the time so we just needed a place to sleep. Parking was a slight issue as there were 4 cars crammed into a steep lot with uneven ground. It met our needs and we would like to return."
United States
Steven
The price is ￥22,793
￥34,181 total
includes taxes & fees
May 26 - May 27
Wine Alley West Suite
Exterior detail

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

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is ￥35,651
￥44,095 total
includes taxes & fees
May 26 - May 27
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Dining

Wine Alley East suite

Wine Alley East suite
Hermann
9.2 out of 10, Wonderful, (79 reviews)
"Great location "
United States
Scotti
The price is ￥22,793
￥34,181 total
includes taxes & fees
May 26 - May 27
Wine Alley East suite
Smart TV, books

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
McKittrick
10.0 out of 10, Exceptional, (2 reviews)
"Loved this placed, would definitely come back!"
United States
Cody W.
The price is ￥35,651
￥44,095 total
includes taxes & fees
May 26 - May 27
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
Terrace/patio

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

Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
Hermann
10.0 out of 10, Exceptional, (21 reviews)
"Booking and checking were very smooth. The house was very clean and just what we needed."
United States
Bryan C.
The price is ￥38,983
￥50,285 total
includes taxes & fees
May 26 - May 27
Private 2BR Hermann Home w/ Deck + Trolley Pickup - Great Event-Ready Stay!
Exterior detail

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

Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
Hermann
10.0 out of 10, Exceptional, (57 reviews)
"Great place to stay"
United States
Adam
The price is ￥42,441
￥85,340 total
includes taxes & fees
May 26 - May 27
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
Exterior detail

Plenty room for relaxing and downtown location to walk around!

Plenty room for relaxing and downtown location to walk around!
Hermann
10.0 out of 10, Exceptional, (18 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 ￥31,634
￥40,932 total
includes taxes & fees
May 25 - May 26
Plenty room for relaxing and downtown location to walk around!
Books

Kork Haus - Whole house rental in Downtown Hermann

Kork Haus - Whole house rental in Downtown Hermann
Hermann
9.6 out of 10, Exceptional, (25 reviews)
"Nice location!"
United States
Brian P.
The price is ￥35,368
￥65,064 total
includes taxes & fees
May 26 - May 27
Kork Haus - Whole house rental 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.
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Top Montgomery City Hotel Reviews

Capital O Amerihost Inn and Suites Fulton Hwy 54 MO

Capital O Amerihost Inn and Suites Fulton Hwy 54 MO

2/10 Terrible
"There was no breakfast and no pool! Said it needed to be inspected! Towels had blood stains.. deposit was double what the website said"
James 2-night trip
Posted 1 day ago
Capital O Amerihost Inn and Suites Fulton Hwy 54 MO

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?

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! : This vacation home rental outside of Montgomery City offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

What’s there to see and do in Montgomery City?

While you're exploring the area, Graham Cave State Park and The Pinnacle are a couple of picturesque spots to get outside and enjoy nature. New Florence United Methodist Church and Endless Summer Winery 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.