Vacation Homes in Montgomery County

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Featured Vacation Homes in Montgomery County

Outdoor dining
Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast

Hermann
10.0 out of 10, Exceptional, (112)
"Very cute room. Perfect for an overnight stay!"
United States
Angel H.
The price is HK$770
HK$1,305 total
includes taxes & fees
5 Jan - 6 Jan 2026
Gipfel Suite - Himmel Haus Bed & Breakfast
Property grounds
Stunning Lakeside Retreat at Innsbrook w/ Swing, Canoe and 3 Kayaks

Stunning Lakeside Retreat at Innsbrook w/ Swing, Canoe and 3 Kayaks

Wright City
10.0 out of 10, Exceptional, (55)
"Second time staying here, the family of 11 finds it very accommodating for everyone."
United States
Ruth Anne F.
Stunning Lakeside Retreat at Innsbrook w/ Swing, Canoe and 3 Kayaks
Outdoor pool
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

Warrenton
8.8 out of 10, Excellent, (20)
"We had a great time at this location. It was cute, clean, and well maintained."
United States
Chloe A.
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Outdoor dining
The Bittersweet Inn: Brand new 6 bed 5 bath house

The Bittersweet Inn: Brand new 6 bed 5 bath house

Hermann
10.0 out of 10, Exceptional, (82)
"Excellent check in. We had six meals so the kitchen was essential and worked well."
United States
Darra J.
The Bittersweet Inn: Brand new 6 bed 5 bath house
Dining
Archie’s House

Archie’s House

Berger
10.0 out of 10, Exceptional, (35)
"Everything was very nice!!! I highly recommend. "
United States
Mary T.
The price is HK$2,318
HK$3,190 total
includes taxes & fees
7 Dec - 8 Dec
Archie’s House
Dining
Ash Creek Suite - In Downtown Historic Hermann

Ash Creek Suite - In Downtown Historic Hermann

Hermann
9.4 out of 10, Exceptional, (51)
"Met our needs"
United States
Craig C.
The price is HK$973
HK$1,955 total
includes taxes & fees
6 Jan - 7 Jan 2026
Ash Creek Suite - In Downtown Historic Hermann
Interior
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

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

Hermann
9.6 out of 10, Exceptional, (105)
"Check was simple. Area was great. Wifi worked perfectly."
United States
Raymond W.
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Outdoor spa tub
Innsbrook Luxe Escape - 5 bedrooms

Innsbrook Luxe Escape - 5 bedrooms

Innsbrook
10.0 out of 10, Exceptional, (75)
"Property was excellent from top to bottom. Furnishings were of highest quality and every little thing we needed was there. 15 of us spent 4 nights and didn’t have any problems. Highly recommend this property. "
United States
Richard H.
Innsbrook Luxe Escape - 5 bedrooms
Smart TV, fireplace, video games, DVD player
Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!

Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!

Innsbrook
10.0 out of 10, Exceptional, (102)
"The home was perfect! Very nicely updated and had everything we needed stocked. "
United States
Katie C.
Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!
Interior
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

Hermann
10.0 out of 10, Exceptional, (153)
"We had a great time and the accommodations were perfect for us."
United States
Leonore G.
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
Dining
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

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

Hermann
9.6 out of 10, Exceptional, (69)
"My husband and I and 3 other couples enjoyed our stay at this spacious, clean, quaint historic home. It was right in the center of town and we were able to walk to shops, winery, restaurants…"
United States
Michelle M.
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Fridge, microwave, oven, stovetop
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

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

Hermann
10.0 out of 10, Exceptional, (168)
"We had a great stay. The house was comfortable and great location. "
United States
Jane I.
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house
Outdoor dining
Get away from it all

Get away from it all

Foristell
9.6 out of 10, Exceptional, (39)
"Great stay, beautiful home!"
United States
Ryan J.
Get away from it all
Fridge, microwave, oven, stovetop
The Farmhouse Inn: 3 bed, 3.5 whole house rental

The Farmhouse Inn: 3 bed, 3.5 whole house rental

Hermann
10.0 out of 10, Exceptional, (110)
"Quick response from owner. Enjoyed our Stay "
United States
Annette
The Farmhouse Inn: 3 bed, 3.5 whole house rental
Outdoor dining
Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann

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 HK$1,401
HK$1,943 total
includes taxes & fees
7 Dec - 8 Dec
Secluded 2 bedroom home close to Hermann
Fridge, microwave, oven, stovetop
5 bed 2 Bath in Downtown Hermann, MO

5 bed 2 Bath in Downtown Hermann, MO

Hermann
9.8 out of 10, Exceptional, (46)
"Great property in a great location plenty if room for 4 couples to spread out. We would definitely stay there again!"
United States
Jacqueline R.
5 bed 2 Bath in Downtown Hermann, MO
Paper towels
Goodale Haus

Goodale Haus

Hermann
9.6 out of 10, Exceptional, (4)
"overall excellent stay at this property, thank you!"
United States
brooke l.
Goodale Haus
Property grounds
Historic Main Street Cottage

Historic Main Street Cottage

Troy
10.0 out of 10, Exceptional, (36)
"Was in town for an event, it was in walking distance of the down town. Super cute and clean, just loved staying there. Definitely recommend!!"
United States
Kelsey K.
Historic Main Street Cottage
Fridge, microwave, oven, stovetop
Hillside Cottage in Beautiful Downtown Hermann

Hillside Cottage in Beautiful Downtown Hermann

Hermann
9.2 out of 10, Wonderful, (25)
"Check-in easy and kitchen was good"
United States
Stewart H.
The price is HK$1,557
HK$2,839 total
includes taxes & fees
14 Dec - 15 Dec
Hillside Cottage in Beautiful Downtown Hermann
Fridge, microwave, oven, stovetop
The Chicken Coop on Highway H

The Chicken Coop on Highway H

Troy
10.0 out of 10, Exceptional, (17)
"Great place to stay. Beautiful decor. Peaceful, relaxing, great set up, welcoming. Loved the decor. "
United States
Paul G.
The Chicken Coop on Highway H
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montgomery County Hotel Reviews

Best Western Teal Lake Inn

Best Western Teal Lake Inn

10/10 Excellent
"The reservation system was down when we arrived but the front desk manager was a pro in getting our information and into our room while he worked through processing out payment. AWESOMENESS!"
Jeff 1-night trip
Posted 2 days ago
Best Western Teal Lake Inn

Find out more about Montgomery County

Montgomery County Vacation Homes information

Number of reviews
1,325
Accommodation
121 Vacation Homes
Lowest Price
HK$1,305
Highest Price
HK$3,190