Vacation rentals in Montgomery County

Farm Stay+Eclectic Vintage+Fresh Eggs+EV Charge

Our eclectic guesthouse is set on 80 acres of quiet magic, come unplug. Discover fun details in the art-filled interior, 1960s phone booth, and light-filled space boasting vintage finds and plants galore. Collect fresh eggs for breakfast, enjoy coffee on the expansive porch. Wander the flower and vegetable garden, hike the wooded trail, explore the creek & shower under the stars. Slow down, reconnect, recharge. 7mins off I-70, 30mins to Hermann & 50mins to both STL airport and Columbia.

Scenic Natureside Stay Off 70~Best of Both Worlds

Conveniently located 2 mins off I-70 in the small town of High Hill yet nestled beside the woods, this duplex unit offers gorgeous backyard views & a calm setting. Your own fenced area of the backyard & private fire pit are perfect for cozy evenings under the stars, and letting your dog run freely out the back door. Inside you’ll find an oversized, yet cozy 1000sq ft living area that is its own private space with all the amenities of home. Hermann - 20mins Wentzville - 30mins Columbia - 45mins

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!

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.

Boar Creek Guest House-sleeps 15

Lovely Farmhouse close to town, ON the Katy trail. We are located just 5 miles from Hermann. Close to the action and them come home to relax around the fire pit or enjoy the expansive patio. House accommodates up to 15 people. Amenities include Game room in the garage, multiple gathering spaces, a large yard and privacy. Perfect for unplugging, disconnecting and getting back to the basics. House is well appointed but not pretentious. Come with your family or for a friends getaway.

Elevated Woodland Escape

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.

1 Bed 1 Bath suite in Downtown Hermann

1 bed 1 bath suite centrally located in charming downtown Hermann. It is fully furnished with everything you should need. No matter what you're in the mood for: Shopping, dining, coffee, cocktails, it's all right around the corner. The Hermann Trolley is a great way to get around town and we just happen to be on the trolley route! Roku TV for you to login to your favorite streaming service (no cable). Additional 3 bedroom suite available downstairs should you have extra guests.

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.

2nd Street Stay

Welcome to 2nd Street Stay in downtown Montgomery City! This renovated, non-smoking suite features 2 bedrooms (1 queen bed, 1 twin), sofa couch with pull out bed, bath with walk-in shower, a kitchenette, washer/dryer, fast WiFi, 2 smart TVs, and a workspace. Enjoy keyless entry, comfort, and convenience—perfect for business, weddings, or a quick stop through town! Please note: our suite is located close to a train track. Ear plugs and a sound machine are provided.

"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

Small private country home with lake, spa, firepit

Country setting, 3/4 mile from town, house on 20 acres, lake, woods in back round, firepit, spa and BBQ area under pergola. 10 minutes from I-70. 25 minutes to Warrenton, 30 minutes from Hermann, Mo. 50 minutes to Columbia and Wentzville, MO. Great place for a staycation, traveling, work from home, or a vacation. Child and pet friendly with lots of running room.