Montgomery County Holiday Rentals

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Top Holiday Rentals Destinations in Montgomery County

Front of property
The Mercantile on the Katy Trail
The Mercantile on the Katy Trail
4.5 star property
9.8 out of 10, Exceptional, (24)
"Our stay was amazing! We loved being near Katy Trail yet close to Hermann Wine/shopping activities. The property was beautiful & clean!"
United States
Elizabeth
The price is NZ$381
includes taxes & fees
21 Oct - 22 Oct
The Mercantile on the Katy Trail
Property grounds
Country Container Tiny House. Experience peace by the water & native wildlife!
Country Container Tiny House. Experience peace by the water & native wildlife!
2.0 star property
9.8 out of 10, Exceptional, (6)
The price is NZ$227
includes taxes & fees
21 Oct - 22 Oct
Country Container Tiny House. Experience peace by the water & native wildlife!
Bar (on property)
Studio Condo on the Water @ Innsbrook
Studio Condo on the Water @ Innsbrook
9.8 out of 10, Exceptional, (37)
"Had a good golf day wonderful place to stay "
United States
david c.
The price is NZ$319
includes taxes & fees
20 Oct - 21 Oct
Studio Condo on the Water @ Innsbrook
Outdoor spa tub
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort
10.0 out of 10, Exceptional, (67)
"We had a lovely lake weekend getaway - Mandy (the owner) was so responsive and helpful. The chalet is lovely and perfectly situated on a private small lake. Our girls loved every moment of water activities."
United States
Andrea G.
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Riverview Cottage. 5 minute walk to downtown
Cozy Riverview Cottage. 5 minute walk to downtown
10.0 out of 10, Exceptional, (35)
"Cute cottage. Very clean and comfortable. Very quiet and relaxing. We enjoyed our stay. "
United States
Carol S.
The price is NZ$463
includes taxes & fees
20 Oct - 21 Oct
Cozy Riverview Cottage. 5 minute walk to downtown
Exterior
Cozy Cabin in the woods near charming Hermann
Cozy Cabin in the woods near charming Hermann
10.0 out of 10, Exceptional, (2)
"Very secluded and cozy. Perfect for a couples getaway "
United States
Jeremy R.
Cozy Cabin in the woods near charming Hermann
Exterior
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
8.8 out of 10, Excellent, (3)
"This is definitely not your conventional vacation place to stay - a working farm, log cabin portions, modern kitchen appliances hidden in plain sight behind old farmhouse cabinets, eclectic decor that you can spend hours browsing and looking at so many unique items. But it was exactly what I was looking for and everything turned out very well. Thank you!"
United States
Judith A.
The price is NZ$1,184
includes taxes & fees
20 Oct - 21 Oct
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.
Fridge, microwave, oven, stovetop
Peaceful chalet - *new* private beach, WIFI, kayaks
Peaceful chalet - *new* private beach, WIFI, kayaks
10.0 out of 10, Exceptional, (74)
"We had a great time staying at this chalet! It was very clean with great amenities. No need to leave when you can play on the lake, build a fire, cook all meals and relax! Would definitely recommend!"
United States
Teryn E.
Peaceful chalet - *new* private beach, WIFI, kayaks
Fridge, microwave, oven, stovetop
Large Unique 2-Bedroom Gamed Themed Loft
Large Unique 2-Bedroom Gamed Themed Loft
9.8 out of 10, Exceptional, (35)
"great overnight stay in the middle of town on our way to Osage Beach from Chicago"
United States
Brady P.
The price is NZ$360
includes taxes & fees
21 Oct - 22 Oct
Large Unique 2-Bedroom Gamed Themed Loft
Fridge, microwave, oven, stovetop
Wine Alley East suite
Wine Alley East suite
9.4 out of 10, Exceptional, (72)
"Great location and perfect little place for the weekend. Beth had everything we needed for our stay. Will be staying again! "
United States
Nick C.
The price is NZ$368
includes taxes & fees
20 Oct - 21 Oct
Wine Alley East suite
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!
9.8 out of 10, Exceptional, (64)
"It is verry pretty inside, loved the decorations, it had 2 king beds, a great out door area. We loved it because of the location. Its two houses down from the Tin Mill."
United States
Emily B.
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!
Fridge, microwave, oven, stovetop
Glamping with gorgeous sunset views, trolley to all wineries
Glamping with gorgeous sunset views, trolley to all wineries
9.6 out of 10, Exceptional, (8)
"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!"
United States
Belen A.
The price is NZ$400
includes taxes & fees
20 Oct - 21 Oct
Glamping with gorgeous sunset views, trolley to all wineries
Outdoor dining
Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit
Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit
10.0 out of 10, Exceptional, (27)
"A peaceful and relaxing long weekend!"
United States
Michael A.
Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit
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!!
9.6 out of 10, Exceptional, (101)
"Great stay . Perfect for 3 couples. House was exactly as described with a great location. Would 100% stay here again! "
United States
Tara P.
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!
Fridge, microwave, oven, coffee/tea maker
Suite on Schiller
Suite on Schiller
9.8 out of 10, Exceptional, (113)
"Great place to stay and location was perfect."
United States
Keith B.
Suite on Schiller
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
10.0 out of 10, Exceptional, (147)
"We stay here each year for a bike race weekend. We really enjoy the space and the location!!"
United States
Craig W.
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
Property grounds
Private Logcabin All To Yourself With Lake View
Private Logcabin All To Yourself With Lake View
9.8 out of 10, Exceptional, (215)
"We loved it and plan on returning "
United States
Jesse S.
Private Logcabin All To Yourself With Lake View
Terrace/patio
Cozy custom-built Cabin - Lakeside
Cozy custom-built Cabin - Lakeside
10.0 out of 10, Exceptional, (56)
"We really enjoyed our stay. Place is very secluded and had everything we needed for a great weekend away!"
United States
Matt B.
Cozy custom-built Cabin - Lakeside
Exterior
The Judges Fair Way! Beautiful 4 bedroom, 3 bath home that sleeps 13
The Judges Fair Way! Beautiful 4 bedroom, 3 bath home that sleeps 13
9.6 out of 10, Exceptional, (47)
"Beautiful house that accommodated 12 family members very comfortably. "
United States
Debbie W.
The Judges Fair Way! Beautiful 4 bedroom, 3 bath home that sleeps 13
Interior
New - custom-built Treehouse - Twilight
New - custom-built Treehouse - Twilight
10.0 out of 10, Exceptional, (4)
"The twilight cabin was so clean and cozy. We enjoyed our stay. "
United States
Katherine H.
New - custom-built Treehouse - Twilight
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 County Hotel Reviews

Hermann Crown Suites

Hermann Crown Suites

10/10 Excellent
"Everything was wonderful "
Marilyn A 1-night trip
Posted 4 days ago
Hermann Crown Suites

Find out more about Montgomery County

Everything you need to know about Montgomery County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montgomery County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery County holiday rentals we have selected for you start as low as NZ$227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montgomery County rentals

At Expedia, we put the best Montgomery County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montgomery County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.