Vacation rentals with a patio in Hermann

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.

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.

Market Street Cottage For Two

Surround yourself with style in this charming historic cottage. Market Street Cottage welcomes guests with a lovely mix of vintage and modern furnishings, designed to enhance your getaway experience. The cottage is located at 9th & Market, just outside of the downtown area. Don’t want to take the short walk downtown? Just call the trolley & they will pick you up just steps from your door. After a fun-filled day of shopping & wineries, relax on the newly poured patio to enjoy the sunset

Treehouse - Sunrise

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. Books and indoor/outdoor games are a must for staying in. We are also close to wine country for an afternoon of shopping or dining.

Hope’s Cottage

Welcome to Hope’s Cottage! This charming one-bedroom, one-bathroom suite is the ideal spot for couples seeking a relaxing stay. Thoughtfully designed for comfort, the space features a cozy queen bed, a modern bathroom, and a peaceful atmosphere. While there's no kitchen, you'll find a mini fridge, coffee maker, and plenty of great local dining options nearby. Whether you're here for a romantic weekend or a quiet escape, this spot offers the perfect blend of simplicity and comfort.

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.

1857 at the Drayton

⚜️Sleeps up to 6 Guests. Heart of downtown Hermann!⚜️ Our Story: We are the Owners/Super Hosts of the Drayton Guest Suites. Our daughter has graduated college, returned to Hermann as a Special Education Teacher & purchased this home. It was then necessary for her to find a way, to sustain.. 1880 was created! Property Owner is NOT on-site, when “1857” is available for guest rentals. Guests have FULL access to all areas of the home, accept for Owner bedroom & basement.

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.

Laughing Boar | Sleeps 11 Historic Downtown

The Laughing Boar, built in 1872, is nestled in Hermann’s downtown Historic District. This charming home offers 4-bed, 5-bath (3 Full, 2 Half) and sleeps up to 11, with a cozy loft. Walk to the Amtrak Station, shops, museums, restaurants, wineries, and nightlife. Under new ownership, the entire house has been extensively cleaned, new bed linens and towels, and a full refresh was completed in Fall 2024. The Boar is ready to host your next getaway!

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!

The Studio

Come relax, renew and rejuvenate in this peaceful and stylish new space. You will actually be staying on our 11 acre Treehouse BnB property, only four minutes from the adorable German wine community of Hermann. If you desire, you can catch a ride on the trolley to explore all of the fun and unique things to do in town. Or you can just kick back and hang out with nature for a while.