Holiday houses in Montgomery Township

1888 Schoolhouse in Wine Country

Right in the middle of Missouri's wine country, this fully renovated 1888 Schoolhouse lets you explore wineries in the area or just sit on the front porch and wave at the locals. Perfect for two or use the fold out couch for additional guests. Pinckney, Missouri was the county seat of Warren County. Danial Boone once sat on the porch of the County Judge right across the street. This quiet street was once the hub of activity due to the Missouri River, now it is a quiet retreat from the noise.

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.

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!

Eclectic Vintage+Quiet Farm Stay+Fresh Eggs

Our eclectic guesthouse is set on 80 acres of quiet magic, come unplug. For the lover of details, enjoy the cozy art-filled interior, 1960s phone booth, vintage furniture and light-filled space. Your stay will inspire you to slow down, reconnect & recharge. Collect fresh eggs for breakfast, enjoy coffee and a morning soak in our newly added spa. Wander the wooded trail, explore the creek and shower under the stars. 7mins off I-70, 30mins to Hermann & 50mins to both STL airport and Columbia.

Secluded "Heaven": soaker tub, sauna, sunset view

"Heaven" ( 1,512 sq ft, 7 ac) sits on a bluff overlooking the Osage river. An open home with huge full length windows and a sun room. Two porches offer views over the river and to the woods. A soaker tub and sauna are situated in the cabin with a view to the sunset. The cabin is at the end of a secluded forest road. A locked garage is available for small cars. Drive: 15-20 min to Linn for supplies / 30 min to Jeff City / 5 min to public river access. Regretfully no kids under 12 or pets.

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.

Home away from Home

A relaxing and inviting home away from home with everything that you need for your stay in Bowling Green. During your stay here you will enjoy the smart TV, free Wi-fi, and washer and dryer. A comfortable night’s sleep is a given with a brand new mattress on all three beds (queen bed and two twin beds). Located on the north side of town, you are less than 1 mile from Wood’s Smoked Meats and Bankhead’s Chocolates. This is an ideal base for your Pike County, MO visit.

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.

Restful Rustic Comfy Cabin.

Sweet little cabin by a little pond at the edge of the woods. Large sunny windows, real bed, (with room to bed a child or two down on the floor) tea pot, easy chair, composting toilet, AC, WiFi, hiking trails. There's no shower in the Cabin. Our water is from a deep well, tested, certified ... and delicious! There is an above ground pool, trampoline, and a trail down the hill Very child friendly. We maintain a fragrance-free facility, so no air "fresheners".

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

Papa's Cabin - 40 acres & 5 acre lake!

Nestled in a rural country setting amidst Amish country, this spacious and rustic cabin sits on 40 acres, just 3.8 miles from the small town of Middletown, MO. Enjoy a lake for fishing, wide open fields, fire pit areas, and a BBQ space. Though this old cabin is far from fancy, it offers a clean, tidy, cozy and quiet atmosphere, even as we continue renovations and an ideal spot for your next staycation with ample room to explore the outdoors.