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1888 Schoolhouse in Wine Country

Right in the middle of Missouri's wine country, this fully renovated 1888 Schoolhouse lets you explore wineries in the area or just sit on the front porch and wave at the locals. Perfect for two or use the fold out couch for additional guests. Pinckney, Missouri was the county seat of Warren County. Danial Boone once sat on the porch of the County Judge right across the street. This quiet street was once the hub of activity due to the Missouri River, now it is a quiet retreat from the noise.

Crown’s DeFlorin Stone Cottage Downtown/Breakfast

Downtown/St. George Catholic Church Location. Free Buffet Breakfast, Complimentary Drink Tickets, $25 All Day Shuttle Service. A Historic Downtown Stay Overlooking Hermann at the 1880 DeFlorin Stone Cottage Inn. Part of the 1899 Historic Hermann Crown Suites Boutique Hotel Group. This is a Rental ONLY to your Group (1 night weekday stays allowed). WiFi, Cable, TVs.Two Additional DeFlorin Homes are also right next door (Allowing Groups of 24 Guests). Access to Our EV Charging Stations as well!

The Mercantile on the Katy Trail -Vaudeville Suite

Welcome to The Vaudeville Suite – A Historic Loft Experience! Step back in time and immerse yourself in our charming one-of-a-kind Vaudeville loft suite, nestled within the walls of the iconic 1897 Mercantile in the heart of McKittrick. This space, once a vibrant opera house, music hall, and theatre stage, now offers a luxe, unforgettable stay that seamlessly blends history with modern comfort. The open layout includes a cozy sitting area, a well-appointed kitchen, and a plush king-size bed.

1940's River Cottage w/ Hot Tub

Something for everyone! This home is less than 9 mi. from historic Hermann, MO. There you can enjoy several wineries, shops & restaurants. From this property you are just a short walk to the Gasconade River near the MO River. Great boating, fishing & swimming w/ easy boat ramp access & parking. The Union Pacific Railway crosses the river & N. side of town. Gasconade is a small quiet town except for the occasional train or boat going by. At night enjoy stargazing from your private hot tub.

Private 77 Acre Farm Hermann MO - Sleeps 8+

Secluded country escape with an elegant touch! Located just minutes from downtown Hermann, MO. This 3 Bedroom - 2 Full Bath sleeps 7 comfortably, but feel free to bring air mattresses. We will accommodate up to 10 without additional charges. From the moment you step foot on the property you can feel the relaxation. Fully stocked kitchen & gas grill to cook up whatever your heart desires. Relax by the fire pit. It’s just the perfect weekend get-a-way from the city.

Cozy 1882 Farmhouse-10 minutes from Wine Country

Getaway to The Farmhouse located in the quiet country near Hermann, Berger and New Haven. Gather with friends and family where children will enjoy space to run/play in and gathering for s'mores around an evening fire. The area boasts of wineries with weekends of fun themed festivities. Set rate on first two guests $145/night (smart pricing in effect on event weekends) . $55 each additional guest/night. Infant- 2 yrs. free, 3-12 $30/night Pets: $30 each pet/one time charge

Labby's Homestead Farmhouse

Our early 1900s Rustic Farmhouse offers 3-Bedrooms and 2 full bathrooms and the ability to accommodate large groups with a total of 9 beds (1 King / 6 Queens / 2 Twins). Featuring a full-service kitchen with cookware and utensils, living room with 55-in smart TV already connected to our free, secure Wi-Fi, make-up area on the upper level, washer and dryer in the entryway area, front porch, and large private back patio covered for all-year-round entertaining.

1860 Presshaus

Built in the 1860's, this unique two bedroom, two and a half bath home is equipped with a full kitchen, an upper/ lower patio with firepit, and access to your own private wine cellar. We are located in beautiful Hermann, Missouri just minutes to local distilleries and wineries. Enjoy country living at its best! Travel 1/2 mile down a well-maintained gravel road and enjoy one of the most unique places in Hermann, Missouri. You won't be disappointed!!

Crimson Cactus Guesthouse

Located in a peaceful neighborhood, this quaint home is perfect for a relaxing weekend getaway in the heart of wine country. It can accommodate up to four people. The sleeping arrangements are one queen-sized bed, and two twin-sized beds. One of the twins is floor level, as it is part of a trundle bed. Please note: You must list how many guests will be staying so house can be arranged to meet your needs and correct pricing can be reflected.

Oktober Haus 3BDRM in Downtown Hermann

Oktober Haus is a block or two from all the amazing spots that Hermann has to offer like Hermannhof Winery, Tin Mill Brewing, Fernweh Distilling and so much more. With 3 spacious bedrooms with King beds, 2.5 bathrooms, and a full air mattress, it's perfect for a weekend getaway with friends or family. Ideally the space is for 6 people. Built in 2019, our place feels brand-new, clean, and comfortable. The location is unbeatable!

Adorable house! Walking distance from downtown.

Formerly known as the Hoff Haus, this is a beautifully renovated 3 bedroom, 2 bathroom home built in 1910. Located on a quiet street right outside of downtown Hermann, this is a two-story home. Walk to shops and restaurants or, for a fee, have the Trolley (Hermann Trolley Company) pick you up out front of the house. Sleeps up to 8 guests. Please note that some guests have described the steps of our staircase as steep.

"B" Our Guest on Market

Our building was once home to one of the original saloons of early Hermann, known as the Farmers Home. Apartment "B" is located on the second floor. Its a great space for a your trip to Hermann. Fully private apartment, king size bed. The space has potential to adjoin for larger parties. For larger groups check out our other listings... 5th & Market Get Away The Hide Away on Market