Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

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Bungalow in Hermann

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First Street Queen Suite

Enjoy easy access to everything from this centrally located home in the heart of historic downtown Hermann. First Street Guest Suites welcomes guests with a charming mix of vintage & modern furnishings, designed to enhance a memorable getaway experience. The queen suite is located within walking distance to all of the downtown restaurants, bars, and shops, as well as Hermannhof Winery and Tin Mill Brewery. The suite is just steps away from the trolley stop & 2 blocks from the train station.

Top guest favorite

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

5 out of 5 average rating, 46 reviews

4K Ranch - 10 acre property & home near Hermann

Charming 10 acre property and home near Hermann Mo's wine country! Our cozy home offers: 2 bedrooms and full bathroom on the main level with 6 additional beds in the second story loft. Surrounded by picturesque farmland, 4K Ranch invites you to relax, recharge, and explore. Enjoy breathtaking views, complete privacy, and a range of thoughtful amenities, including a private art and play studio that’s perfect for kids (or Adults)! Book your stay today and experience the charm of 4K Ranch!

Top guest favorite

The treehouse is illuminated at night, highlighting its modern architecture nestled among trees. Warm lights glow from the windows, contrasting with the dark sky. Surrounding foliage displays vibrant orange hues, adding a serene ambiance to the outdoor setting.

Treehouse in Hermann

5 out of 5 average rating, 70 reviews

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.

Guest favorite

The living area features a spacious gray sofa paired with a brown recliner. A coffee table sits in the center, surrounded by a colorful area rug. Two blue lamps provide lighting, and a television is positioned on a turquoise console. Natural light enters through the window beside the door.

Guest suite in Rhineland

4.96 out of 5 average rating, 226 reviews

White Wolf Inn Apartment

Whether winery hopping, shopping, or visiting in or near Hermann, attending a wedding in the area or just enjoying the Katy Trail, your stay at the White Wolf Inn Apartment is only a few miles away. (Whole house rentals are available, the White Wolf Inn House is a separate listing.) We are close enough to access the Hermann transportation services and all that Hermann has to offer (about 8 miles from town), but far enough away for you to relax in the quiet of the country.

Guest favorite

A dining area features a light wood table set for two, with red plates and glasses. The kitchen area is located in the background, showcasing white cabinets and a dark countertop. A soft, neutral wall color enhances the spaciousness of the room.

Guest suite in Hermann

4.92 out of 5 average rating, 154 reviews

Suite #1 - 1 Bed 1 Bath in the middle of Downtown

Location, location, location! The Suites on 3rd are right in the middle of the action of charming downtown Hermann. Walk everywhere you need to go. Taking the Amtrak into town? We are only a few blocks away. This listing is for Suite 1 and features 1 bedroom and 1 bath. Roku TV for you to login to your favorite streaming service (no cable) Message me for info on how to book more than one suite. We have 5 total suites with a total of 8 bedrooms. Easy contactless check-in!

Guest favorite

A spacious bedroom features a wooden bed with a checkered blanket and complementary pillows. Large windows allow natural light to fill the room, revealing a wooded view. A sitting area is present with a small table and stools, while a stone fireplace adds warmth.

Treehouse in Jonesburg

4.93 out of 5 average rating, 88 reviews

Cozy Cabin in the Woods - 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.

Guest favorite

A modern kitchen and dining area is displayed, featuring a long wooden table paired with a bench. The kitchen showcases sleek cabinetry, a stove, and stainless steel appliances. Natural light fills the space through multiple windows, enhancing the open and inviting layout.

Home in Hermann

4.94 out of 5 average rating, 137 reviews

Entire 3BR/2BA house w/spacious backyard fire pit

Enjoy this entire **Newly Remodeled**-3 bed/2 bath house. Just minutes away from everything that Hermann has to offer. The outdoor patio is spacious enough for BBQs or outdoor activities. Conveniently located across the street from a grocery store, in case you want to cook in the beautiful kitchen or walk across the street to the delicious Mexican restaurant. Can be picked up by The Hermann Trolley in the Village Market parking lot. This home features a keyless entry.

Top guest favorite

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.

Guesthouse in Hermann

5 out of 5 average rating, 131 reviews

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.

Guest favorite

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.

Home in Hermann

4.91 out of 5 average rating, 110 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.

Guest favorite

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.

Home in Hermann

4.9 out of 5 average rating, 255 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.

Guest favorite

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.

Apartment in Hermann

4.82 out of 5 average rating, 381 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

Top guest favorite

The exterior of a historic stone barn features rugged stone walls and a large wooden door framed by greenery. Windows with dark trim allow natural light, and seasonal flowers in pots add a touch of color to the entrance area.

Barn in Hermann

5 out of 5 average rating, 116 reviews

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.