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

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.

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.

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!!

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!

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.