Holiday rentals with outdoor seating in Hermann

A charming brick exterior is presented with a covered front porch, surrounded by lush greenery and vibrant landscaping. An American flag hangs prominently by the entrance, while the scenic surroundings feature a clear blue sky and ample sunlight.

4.92 out of 5 average rating, 178 reviews

French Hill- Amazing location with the best views!

The historic yet completely updated French Hill is located within a short walk to Downtown Hermann (including the Amtrak station), the newly opened Hermann Farm and less than 300 feet from Hermannhof Winery. With Missouri River views and 2,100 sf of living space, it is the ideal place for up to 8 guests to enjoy their stay. No other property in Hermann has this perfect combination of location, amenities and views. We take great pride in our property and it is impeccably clean and maintained.

4.96 out of 5 average rating, 280 reviews

A dining area features a wooden table surrounded by dark chairs, with a vibrant red floral centerpiece. Above, a chandelier made from red glass adds a warm glow. A painting of a woman with an umbrella enhances the wall, complemented by a glimpse of a bathroom in the background.

Loft in Hermann

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.

5 out of 5 average rating, 203 reviews

The farmhouse exterior features a two-story structure with a rusted metal roof, flanked by large trees. A welcoming front porch is highlighted by a red railing and equipped with several chairs, offering a relaxing space to enjoy the surrounding green lawn and peaceful countryside.

Farm stay in Berger

Cozy 1882 Farmhouse-10 minutes from Wine Country

Getaway to The Farmhouse located in the quiet country near Hermann, Berger and New Haven. Gather with friends and family where children will enjoy space to run/play in and gathering for s'mores around an evening fire. The area boasts of wineries with weekends of fun themed festivities. Set rate on first two guests $145/night (smart pricing in effect on event weekends) . $55 each additional guest/night. Infant- 2 yrs. free, 3-12 $30/night Pets: $30 each pet/one time charge

5 out of 5 average rating, 149 reviews

A cozy sleeping area features a spacious bed with a light-colored quilt, accented by a soft turquoise headboard. Two bedside lamps provide ambient lighting, while a decorative tray sits on the bed. Warm wooden accents complement the neutral color palette.

Guest house in Hermann

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.

A spacious kitchen features a large farmhouse sink situated below a window framed by natural stone walls. Wooden countertops complement the dark cabinetry. A view of the outdoors is visible through the window, enhancing the kitchen's inviting space.

4.91 out of 5 average rating, 118 reviews

Labby's Homestead Farmhouse

Our early 1900s Rustic Farmhouse offers 3-Bedrooms and 2 full bathrooms and the ability to accommodate large groups with a total of 9 beds (1 King / 6 Queens / 2 Twins). Featuring a full-service kitchen with cookware and utensils, living room with 55-in smart TV already connected to our free, secure Wi-Fi, make-up area on the upper level, washer and dryer in the entryway area, front porch, and large private back patio covered for all-year-round entertaining.

A charming two-story home is showcased with a gray exterior and maroon trim. The front porch is accessible by a set of stone steps, surrounded by a well-maintained lawn and garden. Partly cloudy skies and trees are visible in the background.

4.93 out of 5 average rating, 148 reviews

Adorable house! Walking distance from downtown.

Formerly known as the Hoff Haus, this is a beautifully renovated 3 bedroom, 2 bathroom home built in 1910. Located on a quiet street right outside of downtown Hermann, this is a two-story home. Walk to shops and restaurants or, for a fee, have the Trolley (Hermann Trolley Company) pick you up out front of the house. Sleeps up to 8 guests. Please note that some guests have described the steps of our staircase as steep.

4.98 out of 5 average rating, 110 reviews

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 kitchen showcases a sleek design with white cabinetry and modern appliances. A farmhouse sink is positioned beneath two large windows, enhancing natural light. Decorative elements include a banner reading 'COFFEE' and woven wall baskets, creating a functional and inviting cooking space.

4.91 out of 5 average rating, 267 reviews

The Schneider House #1 Downtown

Freshly renovated, urban farmhouse vibe conveniently located bungalow style home. Enjoy all of the modern farmhouse finishes of this 3 bedroom 2 bathroom home. Right next to the outdoor amphitheater. Located in the heart of Hermann with dinning, shopping and entertainment all less than 2 blocks away! Only four blocks from the Amtrak station, wineries, breweries and so many more attractions.

The entrance to Apartment B features a white door with a circular sign denoting the apartment number. Two black chairs with a small welcome mat are positioned on the wooden deck, beneath textured red brick walls. Soft light is provided by a wall-mounted fixture.

4.83 out of 5 average rating, 395 reviews

"B" Our Guest on Market

Our building was once home to one of the original saloons of early Hermann, known as the Farmers Home. Apartment "B" is located on the second floor. Its a great space for a your trip to Hermann. Fully private apartment, king size bed. The space has potential to adjoin for larger parties. For larger groups check out our other listings... 5th & Market Get Away The Hide Away on Market

A charming one-story house is seen with a stone and siding exterior. A well-maintained pathway leads to the front door, flanked by manicured bushes. Two windows provide natural light to the living space, while a small porch area offers a seating option.

4.95 out of 5 average rating, 152 reviews

A Romantic Getaway for two in Historic Hermann, MO

Park View Guest Haus is a private "Whole House Rental ". This rental is a relaxing retreat overlooking the Hermann City Park and is within walking distance to Stone Hill Winery, Vintage Restaurant, and a short walk to the Downtown Area. A perfect " Romantic Getaway" for two. No need to interact with other guest, for you will have the whole house to yourself.

5 out of 5 average rating, 106 reviews

A charming cottage features a white exterior with green accents and a sloped roof. Flower boxes adorn the windows, and two decorative black sculptures stand on either side of the entrance. Lush trees frame the property, enhancing the inviting streetscape.

Cottage in Hermann

2- Bedroom Whole House Rental- Downtown Location

Located at 106 Schiller Street, The Vine Suites is just steps away from restaurants, the train depot, trolley, wineries, shops, museums, and more. The four-room property is a modern-day cottage with 2 king beds, full kitchen, private gazebo, and off street parking. You’ll find everything you need to make your visit complete.

A cozy living area is presented, featuring a light wooden floor and soft grey walls. A bookshelf filled with books stands against one wall, while a television and entertainment unit are positioned nearby. A warm lamp casts a gentle glow, complemented by a red armchair and a coffee table.

4.94 out of 5 average rating, 122 reviews

Hilltop Getaway

Cozy, modern-decor home nestled in the Hermann Hills. Located on the Trolley route and close to downtown and all of its attractions, such as wineries, bars, restaurants, and antique shops. Have the entire home to yourselves so you and your significant other and/or friends can enjoy a relaxing trip with plenty of privacy.

Popular amenities for outdoor seating rentals in Hermann

Kitchen

Wifi

Free parking on premises

Air conditioning

House rentals with outdoor seating

A leather sectional sofa is paired with decorative pillows and a cozy throw. A marble coffee table features a decorative arrangement. A large wall art piece hangs above the sofa, and natural light filters in through sheer curtains, enhancing the inviting atmosphere of the living area.

4.98 out of 5 average rating, 51 reviews

Boutique Guest house in Hermann

4.92 out of 5 average rating, 13 reviews

Epic A-Frame! Rooftop, Theater, Hot Tub and Sauna

A cozy living room is highlighted by wooden walls and a warm ceiling light. A soft sofa and two wicker chairs are arranged around a coffee table. Natural light filters in through a window dressed with lace curtains, creating a welcoming gathering space.

4.82 out of 5 average rating, 130 reviews

Hillside Cottage - Whole house in downtown Hermann

A comfortable living area is presented with two navy blue sofas facing each other, accompanied by two covered ottomans. A light overhead fan circulates air in the spacious room, while the kitchen area is visible in the background, featuring modern appliances and warm wooden accents.

4.77 out of 5 average rating, 13 reviews

Hermann Retreat on Massas Creek

The historic stone cottage with red roofing is framed by a white picket fence. A covered porch with seating is visible, with greenery climbing the structure. The clear blue sky provides a vibrant backdrop, highlighting the charming architectural features of the home.

4.82 out of 5 average rating, 231 reviews

Crown’s DeFlorin Stone Cottage Downtown/Breakfast

An expansive deck features comfortable seating options with views of the surrounding greenery. A dining set is positioned under the shade for outdoor meals. Ceiling fans provide airflow, and the landscaped yard extends into the distance, framed by tree-lined hills.

4.99 out of 5 average rating, 133 reviews

Countryside Guest Haus!

The exterior of the brick guesthouse is highlighted, featuring large windows with black shutters. A paved walkway leads to the entrance, flanked by well-placed greenery and a small seating area. A trellis adds character, complementing the charming neighborhood setting.

5 out of 5 average rating, 20 reviews

Hope’s Guesthouse

4.93 out of 5 average rating, 40 reviews

A welcoming exterior of a spacious home is seen, featuring a classic porch with white railings. Lush green bushes and grass surround the entrance, while a clear blue sky with a few scattered clouds enhances the outdoor setting.

Home in New Florence

Spacious Five Bedroom Country Home near Hermann MO

Apartment rentals with outdoor seating

A spacious living area features wooden flooring and a patterned area rug. Seating is provided by a plaid armchair and a sofa, while a coffee table with decorative items is centered between them. Natural light enters through multiple windows, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 12 reviews

Library at Schiller Suites

The kitchen area features modern appliances, including a stove and refrigerator. A wooden countertop provides space for dining, accompanied by three stools. Above, wine glasses hang, adding a functional and decorative touch. The adjoining living space includes a sofa and two chairs, with natural light enhancing the ambiance.

4.64 out of 5 average rating, 156 reviews

Wine Alley West Suite

A sunlit exterior view of a single-story duplex showcases a well-maintained facade with light beige siding. Green shrubs and flowers enhance the entrance, complemented by a small porch with a rail. A gravel driveway provides ample parking space in front of the property.

4.85 out of 5 average rating, 188 reviews

Suite Simplicity~C

The sleeping area features two plush queen-size beds dressed in soft linens adorned with floral patterns. A nightstand with a lamp provides soft lighting, complementing the warm wood flooring and the textured, striped walls that create a cozy ambiance.

5 out of 5 average rating, 4 reviews

The Mercantile on the Katy Trail - The Katy Suite

A row of charming duplex units is set along a gravel path. Each unit features a spacious covered porch with white railings, framed by neatly trimmed bushes and green landscaping. The bright blue sky with scattered clouds enhances the welcoming appearance of the exterior.

4.98 out of 5 average rating, 63 reviews

Suite Simplicity~D

The living room features exposed brick walls and a hardwood floor. A comfortable sofa with decorative pillows and a lounge chair are positioned around a low coffee table, complemented by a light source from a floor lamp. Natural light enters through a window, enhancing the space.

4.98 out of 5 average rating, 80 reviews

the Drayton - Guest Suite “C”

A cozy bedroom features a spacious bed with a light blanket draped over it. Two teal chairs are positioned near a round rug, while a dark wooden dresser complements the floral wallpaper. Natural light filters through sheer curtains, illuminating the inviting space.

5 out of 5 average rating, 6 reviews

Nature's Nook ~ Zia, Hermann

A spacious living area features deep red walls and hardwood floors. An ornate wooden cabinet stands against one wall, while a light-colored couch is positioned near a round coffee table. Sunlight filters through nearby windows, illuminating the room's vintage decor.

4.78 out of 5 average rating, 9 reviews

Alsace Suite at Schiller Suites

Other holiday rentals with outdoor seating

A two-story house features a covered front porch with white railings. Natural light bathes the exterior, highlighting the beige siding and dark red roof. A sign reading 'Welcome' is positioned near the entrance, complemented by a gravel area and green landscaping.

4.92 out of 5 average rating, 37 reviews

Britton Haus on 6th! 5 beds, 2 baths Downtown

4.85 out of 5 average rating, 88 reviews

The WRIGHT PLACE to stay in Hermann, Missouri!

A spacious deck is presented with a wooden floor and a seating arrangement featuring a central fire pit. Four black wicker chairs with teal cushions are placed around the fire pit, complemented by a matching chaise lounge, creating an inviting outdoor relaxation area.

4.94 out of 5 average rating, 17 reviews

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

A modern exterior of a studio apartment is seen, framed by lush greenery. White siding contrasts with the forest backdrop. A welcoming bench sits by the door, alongside two potted shrubs. The gravel path leads to the entrance, inviting guests to explore the serene surroundings.

4.96 out of 5 average rating, 23 reviews

The Studio

The exterior of a welcoming brick house features a spacious front porch with seating, surrounded by green foliage. Large windows provide natural light, and a clearly marked sign indicates the property's name. A gentle slope leads up to the main entrance.

4.91 out of 5 average rating, 43 reviews

215 Market Street, Hermann, MO 65041, Whole House Rental

4.91 out of 5 average rating, 105 reviews

A charming exterior is showcased with a covered patio featuring two small tables surrounded by flowers in planters. The property overlooks a tranquil lake, with trees visible in the background and a spacious area for parking in front.

Loft in New Haven

Lakefront Studio Guest Home on Hermann Wine Trail!

5 out of 5 average rating, 52 reviews

An aerial view showcases a charming home with a red metal roof, surrounded by lush green fields and distant hills. A gravel pathway leads to a small outbuilding, while a tree with vibrant red foliage is positioned in the front yard.

Home in New Florence

4K Ranch - 10 acre property & home near Hermann

The exterior of a charming two-story home is presented, featuring white clapboard siding with detailed trim. A covered porch with white railing frames the entrance, while large windows allow natural light to enter. The green roof adds a subtle contrast to the overall design.