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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.

4K Ranch - 10 acre property & home near Hermann

Charming 10 acre property and home near Hermann Mo's wine country! Our cozy home offers: 2 bedrooms and full bathroom on the main level with 6 additional beds in the second story loft. Surrounded by picturesque farmland, 4K Ranch invites you to relax, recharge, and explore. Enjoy breathtaking views, complete privacy, and a range of thoughtful amenities, including a private art and play studio that’s perfect for kids (or Adults)! Book your stay today and experience the charm of 4K Ranch!

Roam Suite at Brickhouse Inn

The Roam Suite at the Brickhouse Inn is close to everything, making it easy to plan your visit. Just a block from the train station, close to all the downtown coffee shops, restaurants, and boutiques. Hop on the trolley just a block away. Free parking. This suite has a king bed with new Serta mattress and a living room with a queen sleeper sofa. Full kitchen with gas stove in the suite, as well as two TVs. Large backyard with patio furniture to sit outside and enjoy a beautiful evening.

Hermann Whitetail Farmhouse

A modern farmhouse-styled rental home located south of historic Hermann, Missouri. Full use of large acreage property with lake area surrounded by forest. Quiet and secluded, but within minutes of downtown Hermann. Full kitchen, multiple dining areas, and HUGE entertaining area with pool table, games, TV's and bar. Private bedrooms and large bunk-bed room that sleeps four. Perfect for large groups or your next celebration. Stay for a weekend or a week with Hermann Trolley service available.

Elevated Woodland Escape

We strive to provide you with a unique getaway experience with an escape into nature on Whispering Pine's hundred acre farm...leaving the stress of everyday life behind while you can invest and reconnect with yourself and your loved one! We provide a full kitchen, hot tub, floor-to-ceiling fireplace, luxury bathroom, laundry room and firepit for your use. We are also close to wine country for an afternoon of shopping or dining. Enjoy the lovely setting of this romantic spot in nature.

Cozy Hermann Home that is IN TOWN!(sleeps 10)

This rental is close to the downtown area. (1 mile) The trolley will pick you up right next to the house. There are 3 bedrooms, 2 full bathrooms, a living room with a fold out murphy bed, a kitchen, a screened in patio and a deck with a sitting area and fire pit We are on a quiet cul-de-sac street. We are also next to Caseys (1 minute walk) so you can easily grab snacks or things you forgot. This rental is for the top level of house. The bottom level of house is a separate unit.

the Drayton guest suites - "Suite B" - 109 E. 4th

"Suite B" ----------- - Suitable for Up to 4 Guests - 1st Floor - 1 Queen Bed - Door May be Closed in the Bedroom for Privacy or Left Open with a Large Drapery Divider Between the Bed and Walk-Thru Hallway - 1 Living Room w/Queen Sofa Sleeper - 1 Smart TV w/Apps - * Guests may log into their own accounts, ie. Netflix, HBO, etc.* - 1 Mini- Kitchen w/Mini Fridge, Microwave, Keurig Coffee Maker - 1 Full Bathroom w/100 Year Old Clawfoot Tub/Shower Combination - Front Patio Seating

Out On A Limb Treehouse

A unique Treehouse, 6 miles from Hermann, MO, offers a luxury escape with stunning views and sunsets. Perched on stilts by Daniel Boone Conservation Area, enjoy tranquility, hiking, and wildlife. Relax in a king-size bed beneath skylights, soak in a tub, or unwind in the hot tub and firepit. Just a mile from the Katy Trail, perfect for cycling or relaxing. Explore Hermann’s wineries, shops, and events. Transportation available from Hermann Trolley, Uber & Lyft. Sleeps 2 adults.

Apothecary Guesthaus

Built in 1876 as a pharmacy, this freshly renovated historic building is the ideal guesthaus. Relax on the large deck overlooking the river, or explore the wineries + distilleries all within walking distance. Sleeps 6 with plenty of space for everyone to relax. Primary suite has king bed, private bath, and sitting area. Two other bedrooms include queen beds with a common bath suite. Living area with 2 couches + 2 chairs is the perfect place to relax after a day at the winery.

Das Hundehaus-Downtown Location-Off Street Parking

Das Hundehaus is centrally located in Hermann's downtown historic district on East 2nd Street. The cottage is conveniently located just steps away from restaurants, shops, museums, and more. The cozy cottage offers an open concept floor plan featuring a full kitchen, king bed, sitting area, private bathroom with large shower and off street parking. Start your mornings with a cup of coffee on the private deck and end your evening relaxing with a glass of wine.

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!!

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!