Holiday houses in High Hill

The Downtown Hermann Hen House Food/Bar/Music/Fun

Free Buffet Breakfast/Free Drink Tickets/Live Music Nightly through Oct./Personalized $20 Per Person Shuttle (Trolley is $30)1837 Bar/Restaurant. Put All Your Eggs in the Hen House’s Basket. Right by Restaurants/Shopping/Bars. 2 Bedrooms, 2 Private Bathrooms, & 2 Queen Pullout Sleepers in Living Room. Room for 8 Guests. Full Kitchen & Large Farm Table for Dining or Games with Your Friends. Property Managed by the Hermann Crown Suites next door. Call Hermann Crown to Reserve Spot on Shuttle Now.

The Bittersweet Inn: Brand new 6 bed 5 bath house

Plenty of room for everyone in this brand new house. The Bittersweet Inn is a 6 bed, 5 bath house perched perfectly on a hillside with a picturesque view of beautiful Hermann, MO. The entire house has been decked out in mid century modern decor. The lower level features a bar w/ a second full size refrigerator so guests on both levels of the house will have a place to relax. Parties or events not allowed. Easy contactless check-in! Roku for you to login to your streaming service (no cable).

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

1940's River Cottage w/ Hot Tub

Something for everyone! This home is less than 9 mi. from historic Hermann, MO. There you can enjoy several wineries, shops & restaurants. From this property you are just a short walk to the Gasconade River near the MO River. Great boating, fishing & swimming w/ easy boat ramp access & parking. The Union Pacific Railway crosses the river & N. side of town. Gasconade is a small quiet town except for the occasional train or boat going by. At night enjoy stargazing from your private hot tub.

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.

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.

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 $166/night (smart pricing in effect on event weekends) . $63 each additional guest/night. Infant- 4 yrs. free, 5-12 $30/night Pets: $30 each pet/one time charge

Celestial Log Cabin on the Confluence

Fantastic Eagle Watching! Enchanting 1940's log cabin overlooks the confluence of the Missouri & Osage rivers in charming Bonnots Mill, MO. Close to Columbia, Hermann & Jeff City. Includes master bedroom, open loft, wood-burning hearths, chef's kitchen, clawfoot tub. Double deck overlooking the confluence is a stargazers dream. Secluded, surrounded by nature, find yourself restored after hiking, antiquing, cooking or drinking wine and taking in the beautiful surroundings

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.

Spacious 6BR Retreat | Near I-64 & Weddings

Enjoy a comfortable stay in this modern smart home near Highway 64, ideal for families, groups, and guests attending nearby weddings. Cook in a fully equipped gourmet kitchen, enjoy eight 4K smart TVs, reliable WiFi, and a dedicated workspace for remote work, all enhanced by smart technology for added comfort and ease. Conveniently located near dining, shopping, and popular attractions, and just 30 minutes from STL Airport, it offers a smooth, spacious, and inviting stay.

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.

Charming tiny home - Nova’s House

Reconnect with nature at this tiny home on a working horse facility. Enjoy sitting outside on the patio, starting a fire in the fire pit, or watching deer and turkey wander by. If you are so inclined to interact with horses, we offer both riding and ground lessons for beginners to advanced - Maplewood Farm has been in business for almost 30 years! Located just 5 miles from Fulton, MO and only 20 miles from Columbia, MO and easy access to I70 and Hwy 54