Holiday 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.

Rhine Suite at Brickhouse Inn

The Rhine 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. Plenty of 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 TVs. 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

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.

Cozy Cabin - Lakeside

Imagine being transported to a place far from the demands of daily life and being able to reconnect with nature and those you love. Close enough for a quick getaway, yet far enough to escape the everyday grind. We are so excited to share with you our idyllic cabin on 100 beautiful acres filled with tree-covered ridges overlooking scenic valleys with tall pines, private hiking trails that seem to whisper in the wind while overlooking a private lake. Close to wine country.

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!!

Jefferson Street Hideaway

Enjoy a cozy experience in the heart of Hermann, MO. Accommodations are in the newly renovated, private basement of my home with private entrance & all the luxuries of home. We are located down the hill from Stone Hill Winery and walking distance to downtown. Hermann Trolly picks up right in front of house for transportation to all other wineries and tourist locations. Pets do live on this property so you may hear our dog bark.

the Drayton Guest Suite - "Suite D", On 2nd Floor

Suite D sleeps up to 4 and is located on the 2nd Floor, via the iron spiral staircase. See photo. - 1 Queen Bedroom - 1 Living Room w/Queen Sofa Sleeper - 1 Smart TV w/Apps in Living Room * 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/Tub/Shower Combination - Front Patio Seating

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.

Sage Guesthouse

Take it easy at this unique and tranquil getaway. Enjoy the peace and quiet of the country after a bustling day touring, tasting, shopping, and exploring Hermann. The deck will provide a great view of the rolling hills and a working angus/hereford century old cattle farm. The late evenings will provide a star filled sky for the eyes to gaze for their favorite constellation!