Holiday rentals with a fireplace in Hermann

Magnolia Inn

Adorable 3 bedroom 2 bath house with a modern farmhouse vibe. There are 2 king beds and a queen bed in 3 bedrooms. The queen bedroom has an en suite full bathroom, one of the king bedrooms has an en suite half bath, and there is another full bath in the hall. Amazing outdoor space with a stylish covered patio. Huge open main living area perfect for hanging out when you're not busy winery hopping. Queen sleeper sofa in the living room to accommodate extra guests. Walking distance to Stonehill Winery or have the popular Hermann Trolley pick you up right from the house! The base price is for up to 6 people (2 people per room). For more than 6 people, there is a $25 per person, per night extra guest fee. Roku TV for you to login to your favorite streaming service (no cable).

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.

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 - Twilight

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.

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.

Half Corked Inn-Location and Comfort in one!

BEST LOCATION IN HERMANN! RIGHT ON 1ST STREET. Trolley across the street. Walking distance to brewery, Hermannhoff winery & farm, shops, restaurants, bars, etc. Train station 1 block away. Close to the Katy Trail. Silver Moon loft is cozy with beautiful decor and comfortable beds with clean bathrooms, stocked kitchen, inviting living room. Roomy and very clean. Courtyard and firepit. 2 Breakfast coupons at Stomp'n Grounds a thank you from us to you to use during your stay.

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.

Hope’s Guesthouse

At 108 Schiller Street Hope’s Guesthouse offers the perfect blend of comfort and convenience, just steps away from restaurants, the train depot, trolley, wineries, boutique shops, coffee shops, museums, and more. This charming two-room house features two cozy queen beds, a fully equipped kitchen, and a spacious side yard—providing everything you need for a relaxing and memorable stay. Whether you're here to explore or unwind, Hope’s Guesthouse is your ideal home away from home.

Olive Hutch Upstairs Apartment

Enjoy a stylish experience at this centrally-located upstairs suite. Private entrance from street and off street free parking available. This suite is brand new but located in a historic building. 2 Bedrooms both home to king size beds, with a Murphy bed queen sleeper in the living room. Full kitchen and large bathroom with laundry room in suite. Steps away on the same street as trolley stop, live music, piano bar, great restaurants, shopping, and more!

Converted grain bin guest house on Katy Trail.

Rustic charm with modern amenities and comfort. King bed in upstairs loft with walkout balcony. Modern kitchen with refrigerator ice maker, convection oven/stove, dishwasher and microwave. It’s the perfect escape for two to enjoy the unique charm located next to farmhouse that is available as additional lodging for 8. Hermann is a short 12 minute drive or choose transportation options from Hermann to get you to and from.

First Creek Hideaway | Fire Pit | Wine Country

Enjoy the peace and quiet of the country while being just a short drive from downtown Hermann and its many local wineries, restaurants, and shops. First Creek Hideaway is calling your name to spend the weekend if you're in town for a girl's trip, friend's trip, wedding, or just a weekend getaway. The house was designed with your comfort and convenience in mind while experiencing all Hermann has to offer!

The Barn at Schon Stein Farm & Vineyard

Nestled in the hills & bluffs above Hermann, the Stone Barn at Schon Stein Farm & Vineyards takes you back in time in this historic wine press barn that has been carefully restored and decorated with primitive period antiques...situated on 20 acres in the bluffs with beautiful views! The town of Hermann is minutes away down the hill, and trolley pick up is available.