Holiday Rentals in Montgomery County

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Featured Holiday Rentals in Montgomery County

The Mercantile on the Katy Trail

4.5 star property
Hermann
9.8 out of 10, Exceptional, (28)
"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 €209
includes taxes & fees
17 Nov - 18 Nov
The Mercantile on the Katy Trail

Studio Condo on the Water @ Innsbrook

Wright City
9.8 out of 10, Exceptional, (39)
"Had a good golf day wonderful place to stay "
United States
david c.
The price is €161
includes taxes & fees
16 Nov - 17 Nov
Studio Condo on the Water @ Innsbrook

Country Container Tiny House. Experience peace by the water & native wildlife!

2.0 star property
Fulton
9.8 out of 10, Exceptional, (11)
"A good place to unwind"
United States
Don
The price is €116
includes taxes & fees
16 Nov - 17 Nov
Country Container Tiny House. Experience peace by the water & native wildlife!

Cozy Riverview Cottage. 5 minute walk to downtown

Hermann
10.0 out of 10, Exceptional, (41)
"Was such a cute cottage! We had a wonderful stay and it was just as described! I would definitely stay there again. "
United States
sherri s.
The price is €235
includes taxes & fees
16 Nov - 17 Nov
Cozy Riverview Cottage. 5 minute walk to downtown

Wine Alley East suite

Hermann
9.4 out of 10, Exceptional, (75)
"Great location "
United States
Barry
The price is €187
includes taxes & fees
17 Nov - 18 Nov
Wine Alley East suite

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

Hermann
9.8 out of 10, Exceptional, (66)
"The house was beautiful! Perfect for a girls weekend and so close to the best slushies I’ve ever had! I hope to stay here again! "
United States
Carlie B.
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort

Innsbrook
10.0 out of 10, Exceptional, (69)
"We absolutely loved staying at the Cozy Chalet! It was clean, decorated so cute, and perfect location. We will be back this summer!"
United States
Whitney U.
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort

Peaceful chalet - *new* private beach, WIFI, kayaks

Innsbrook
10.0 out of 10, Exceptional, (76)
"The property was great for what we needed and Mike was very responsive whenever we had any questions"
United States
rachel h.
Peaceful chalet - *new* private beach, WIFI, kayaks

Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

New Haven
8.8 out of 10, Excellent, (3)
"This is our second stay at this beautiful property. We rang in the New Year at Mandolin Ridge and it was beautiful. We were greeted with the birth of two baby goats which was quite auspicious. The home is spacious and like going to a comfortable, beautifully appointed museum. Each room has hidden delights. A feast for the eyes indeed. The host, Loribeth, is considerate and warm as well detail oriented. It is clear she wants to provide excellence! Mandolin Ridge and Loribeth really deliver."
United States
Julie P.
The price is €608
includes taxes & fees
15 Dec - 16 Dec
Mandolin Ridge Farm—Log Cabin Luxe! Pet Friendly. Livestock Guard Dogs Onsite.

Glamping with gorgeous sunset views, trolley to all wineries

Berger
9.6 out of 10, Exceptional, (9)
"Property was nice. Close enough to downtown Hermann but far enough away from the noise."
United States
Amanda O.
The price is €203
includes taxes & fees
16 Nov - 17 Nov
Glamping with gorgeous sunset views, trolley to all wineries

Lakefront Studio Condo

2.0 star property
Wright City
9.6 out of 10, Exceptional, (20)
"The place is exactly as described. It was very clean and offered everything you would need for a weekend stay. The back porch looks out to a lake, and we were within walking distance of a great spot for the fireworks. We'd stay here again. "
United States
ali l.
The price is €215
includes taxes & fees
16 Nov - 17 Nov
Lakefront Studio Condo

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

Hermann
10.0 out of 10, Exceptional, (152)
"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

Private Logcabin All To Yourself With Lake View

Hermann
9.8 out of 10, Exceptional, (215)
"Cabin was wonderful. Lake was well stocked, AC worked well, and bed was comfy. Thanks so much!"
United States
sam n.
Private Logcabin All To Yourself With Lake View

Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit

Innsbrook
10.0 out of 10, Exceptional, (29)
"A peaceful and relaxing long weekend!"
United States
Michael A.
Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit

Treehouse - Sunrise

2.0 star property
Jonesburg
10.0 out of 10, Exceptional, (19)
"5 star stay!"
United States
Jennifer G.
Treehouse - Sunrise

Gipfel Suite - Himmel Haus Bed & Breakfast

Hermann
10.0 out of 10, Exceptional, (111)
"The room was very nice. Renee thought of everything we could possibly need. The homemade hot breakfast was excellent. Thank you!"
United States
Stacey W.
The price is €148
includes taxes & fees
17 Nov - 18 Nov
Gipfel Suite - Himmel Haus Bed & Breakfast

Breathtaking Views + Private Beach

2.0 star property
Innsbrook
10.0 out of 10, Exceptional, (7)
"Our family had a great time at the chalet. We loved the view and caught several different types of fish!!"
United States
Emily E.
Breathtaking Views + Private Beach

Ash Creek Suite - In Downtown Historic Hermann

Hermann
9.4 out of 10, Exceptional, (51)
"Good location and accommodations"
United States
Angie O.
The price is €222
includes taxes & fees
1 Dec - 2 Dec
Ash Creek Suite - In Downtown Historic Hermann

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

Warrenton
8.8 out of 10, Excellent, (20)
"We enjoyed our family get together in the house. Only down side was the grass was quite tall & the little kids couldn’t play in the grass due to mosquitoes. The upstairs bathroom had no hot water to shower. We spent most of our time in outdoor space. Would definitely recommend this property as it met our needs & we spent most of our time enjoying the pool."
United States
Susan T.
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

Newly remodeled home in Historic Hermann Wine Counrtry.

Hermann
10.0 out of 10, Exceptional, (77)
"Great town to visit and the house was perfect for the trip."
United States
Jake B.
The price is €684
includes taxes & fees
1 Dec - 2 Dec
Newly remodeled home in Historic Hermann Wine Counrtry.
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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Holiday Homes in Montgomery County

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