Vacation rentals in Montgomery County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montgomery County

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

Home in New Florence

5 out of 5 average rating, 40 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 kitchen features a sleek black countertop complemented by a hexagonal tile backsplash. Natural light enters through the window, which has blinds. Shelving holds cooking essentials, while modern appliances, including a microwave and a refrigerator, are neatly arranged for convenience.

Treehouse in Jonesburg

5 out of 5 average rating, 19 reviews

NEW Treehouse - Sunrise

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. Books and indoor/outdoor games are a must for staying in. We are also close to wine country for an afternoon of shopping or dining.

Top guest favorite

The exterior of a brick building is shown, featuring large windows and a welcoming sign reading 'Hermannhoff.' The surrounding area includes a driveway and green shrubbery, with trees partially visible in the background under a cloudy sky.

Loft in Hermann

4.96 out of 5 average rating, 256 reviews

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.

Top guest favorite

Treehouse in Hermann

5 out of 5 average rating, 42 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.

Superhost

A hallway is visible, featuring warm wooden trim and a potted plant in a woven basket. An inviting seating area is seen to one side, with a decorative pillow on the bench. A doorway leads into another room in the background.

Apartment in Hermann

4.89 out of 5 average rating, 134 reviews

Piano Bar Suite 4 - 1 Bed, 1 Bath, Full Kitchen

The Piano Bar Suites are located in the heart of downtown Hermann, MO at the corner of Market Street (Hwy 19) and 4th Street. The suites are located above The Piano Bar and all guests to the Suites will receive Hermann Bucks to use in the historic district. This location is ideal for walking and exploring Hermann with restaurants, bars and shopping nearby. Please note, given the prime location in the city center and being located above a bar, there is a higher noise level.

Top guest favorite

Decorative shelves display a variety of bottles and small accents. A green plant is housed in a glass container alongside a brown wooden box, adding texture and color to the neutral wall.

Guest suite in Rhineland

4.96 out of 5 average rating, 218 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 bright bathroom is highlighted by a classic clawfoot bathtub positioned next to a white, patterned shower curtain. Natural light enters through a large window, illuminating the tiled floor and sleek vanity with ample storage and a mirror above.

Guest suite in Hermann

4.93 out of 5 average rating, 148 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 rustic sideboard showcases a coffee maker and decorative mugs, with a collection of canisters labeled for coffee, sugar, and tea. A unique metallic wall art piece resembling a sunburst brings character to the arrangement, set against a neutral wall.

Home in Hermann

4.95 out of 5 average rating, 131 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 galvanized metal bucket contains neatly folded white towels, alongside a navy towel labeled 'makeup.' Accompanying the towels are several tubes of lotion and a round soap, all displayed on a speckled countertop with sunlight filtering through blinds.

Guesthouse in Hermann

5 out of 5 average rating, 118 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.

Top guest favorite

A modern kitchenette features a stainless steel refrigerator and a sleek sink, complemented by white cabinetry. Open shelves display dinnerware and glassware. Countertop appliances are arranged neatly, with a decorative mirror enhancing the space. A large rug is positioned on the floor, adding texture.

Apartment in Montgomery City

4.98 out of 5 average rating, 117 reviews

St Jude's Night Away

This freshly renovated non-smoking suite sits down town Montgomery City. If your traveling through town, in town for business or a wedding-check out our suite. 2 bedrooms, 3 beds, 1 Bath with walk-in shower. Fully equipped kitchenette with full size refrigerator, microwave, induction stove top for cooking. Washer and Dryer. Free Fast and reliable WiFi and 2 smart tv's. Laptop friendly workspace with good lighting. Keyless entry for easy check-in and out.

Superhost

A set of metal stairs leads from a gravel area to a second-floor entrance. The stairs are framed by wooden railings and create access to a balcony adorned with string lights. Potted plants are situated near the base, contributing to the inviting exterior.

Apartment in Hermann

4.82 out of 5 average rating, 371 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 interior living area features exposed stone walls and wooden beams, creating a rustic charm. A cozy seating arrangement with patterned cushions is situated near a wooden coffee table. A staircase leads to an upper sleeping area, with a glimpse of a bed in the background.

Barn in Hermann

5 out of 5 average rating, 113 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Montgomery County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Montgomery County

Guest favorite

A modern bathroom is presented with a circular mirror above a stylish vanity. The sink features a rectangular basin, while the wooden drawer unit is detailed with woven elements. Soft towels are hung on a black ring, and minimalistic wall decor complements the space.

Farm stay in Hermann

5 out of 5 average rating, 5 reviews

NEW! VillaBella Luxury Farmhouse

Karen ERating, 5 stars2 weeks ago

We enjoyed staying at the villa Bella with our family of 7… there were 3 spacious bedrooms, 2 nice bathrooms and all the things we needed to enjoy a fun family time in Hermann Mo. Keren was very helpful and accommodating and we appreciated her letting us stay while we were in town. We would recommend confidently !

Guest favorite

A tranquil outdoor sitting area features a circular arrangement of four Adirondack chairs surrounding a stone fire pit. Lush green grass surrounds the seating, and tall trees provide a natural backdrop. A wooden fence and a view of nearby foliage complete the peaceful setting.

Cottage in Hermann

4.96 out of 5 average rating, 47 reviews

Cozy Riverview Cottage. 5 minute walk to downtown

AlexRating, 5 stars1 month ago

We loved our stay. Jenna’s home is beautiful and we had the best time. The firepit was awesome and we took advantage of it for sure! This is the perfect place to stay for a girls weekend, or for a couple. Some things to note… there is no lock on the bathroom door. We made due by sliding the laundry hamper in front to keep it closed, and it worked great for us! Additionally, the “hill” was DEFINITELY a hill, we were fortunate enough to get a ride from the train station, but it would’ve been quite the hike while hauling our bags. (Recovering from an injury, doable otherwise, especially without your luggage). Lastly, the lock on the front door automatically locks each time it’s closed so just be certain you remember the code, or have your phone with you 😊 Jenna was a great host. Very responsive and kind when answering our questions leading up to our stay, and her instructions were incredibly clear/helpful. Would LOVE to return!! Book with Jenna and you won’t regret it! ☺️

Guest favorite

The exterior of a cozy cottage is illuminated at night, showcasing a welcoming porch with two chairs. A fire pit surrounded by several seating options sits in the foreground, with a gentle smoke rising into the night sky.

Cottage in Hermann

5 out of 5 average rating, 8 reviews

Hanna’s Cottage

PeytonRating, 5 stars6 days ago

Loved Hermann and also the historic vibe of the cottage! Affordable and easy for a couple looking for a last minute place to stay

Home in New Florence

4.85 out of 5 average rating, 13 reviews

John and Jan's Guesthouse clean & peaceful

AbbyRating, 5 stars20 months ago

We stayed here to go to the Oktoberfest celebration in Herman. it was only about 15 min or so away and the drive was beautiful, especially in the fall. The house was very cute and charming! we had everything we needed!

A spacious deck extends from the home, highlighted by sturdy black railings. A grassy area is visible beyond the deck, featuring a solitary tree amid the wooded landscape. The sky above is partly cloudy, allowing for natural light to brighten the space.

Home in Hermann

4.6 out of 5 average rating, 5 reviews

Hermann Retreat on Massas Creek

AnnaRating, 5 stars2 months ago

The drive to the house was gorgeous and the property was peaceful and private. The house was just like the pictures, clean, and well stocked with essentials. We enjoyed the large deck and comfy chairs.

Guest favorite

Home in Hermann

4.97 out of 5 average rating, 35 reviews

The Schneider House #3

AlexandriaRating, 5 stars2 weeks ago

Home was clean and spacious.. walkable to wineries and restaurants. Easy to get in out.. street parking right in front.

The exterior of a red cabin is displayed, featuring a white door at the center. On either side, two bright yellow chairs sit around a small black table, creating a cozy seating area. Potted plants are positioned nearby, enhancing the inviting setting.

Cabin in Hermann

4.91 out of 5 average rating, 45 reviews

Cheerful 1 Bedroom Cottage. Free Parking.

MeganRating, 5 stars22 months ago

Ruth Ann was so sweet and always available! She even offered to drive us into downtown Hermann free of charge, it was the nicest thing. The place was extremely clean and easy to get too and from the different places with rides and such set up! Highly recommend this cute cottage!

Top guest favorite

A screened-in porch features a striped rug over wooden flooring, offering seating with two chairs and a sleek sofa adorned with decorative pillows. Large windows provide views of the surrounding greenery, enhancing the peaceful ambiance.

Home in New Florence

4.91 out of 5 average rating, 35 reviews

Spacious Five Bedroom Country Home near Hermann MO

Lea IsabelRating, 5 stars1 month ago

Our family had a wonderful time at Faith's Haven. It was lovely , clean and well organized. It felt like home. There were plenty of throw blankets, and more appliances than we could use. The porches were great since it rained most of the weekend. It was very to the wedding venue and close to the quaint city od Hermann. Overall, this home was a great choice.

Show all

Vacation rentals in Montgomery County

Top-rated vacation rentals in Montgomery County

Vacation rentals for every style

Popular amenities for Montgomery County vacation rentals

Other great vacation rentals in Montgomery County

Destinations to explore