Vacation rentals in Montgomery County

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.

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!

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.

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.

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.

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.

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.

Suite #2 - 1 Bed 1 Bath in Downtown Hermann

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 2 and features 1 bedroom and 1 bath. Message me for info on how to book more than one suite. Check out my reviews! Easy contactless check-in & only one flight of steps to access.

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 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.

2nd Street Stay - Upstairs Suite

Located in the heart of downtown Montgomery City, this upstairs suite is just a short walk to local restaurants. It features new carpet, a renovated bathroom, full kitchen, washer/dryer—ideal for extended stays. Please note: not kid-friendly due to stairs and low windows. Light sleepers may hear nearby trains. Still, it's a cozy, convenient stay—we’d love to host you!