Vacation rentals in Montgomery Township

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Top-rated vacation rentals in Montgomery Township

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

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Guest favorite

An open-concept living space features a well-equipped kitchen with stainless steel appliances and wooden cabinetry. A large dining table is positioned nearby, complemented by a comfortable seating area with a sofa and armchair. Rustic beams enhance the airy atmosphere of the room.

Guesthouse in Hermann

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.

LocationValueKitchen

4.95 out of 5 average rating, 148 reviews

Top guest favorite

Guesthouse in High Hill

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.

LocationFamilyTV

5.0 out of 5 average rating, 59 reviews

Top guest favorite

Townhouse in High Hill

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

ValueFamilyParking

4.98 out of 5 average rating, 51 reviews

Guest favorite

A private hot tub, designed for four, emits bubbling water under a partially opened cover. The surrounding area includes wooden fencing and a nearby garden chair, creating a secluded space for relaxation.

Cottage in Gasconade

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.

ValueLocationOutdoor spaces

4.91 out of 5 average rating, 312 reviews

Top guest favorite

An inviting pool area is surrounded by stone landscaping, featuring glowing lights along the edges. Comfortable seating includes lounge chairs and shaded areas for relaxation, with lush greenery visible in the background. The in-ground pool reflects the evening sky, enhancing the tranquil setting.

Home in Columbia

Upscale country living at its finest! Pool,HotTub

Nestled onto 10 peaceful acres, w/pond about 15 minutes to downtown Columbia and the University, close to restaurants, and activities, that is if you want to leave the Pool and the quiet of the country. 8 beds, + a few air mattresses, plus 2 pack/plays. You'll love the kitchen, the peace, and the coziness. The in-ground heated pool is 25 x 50 feet. (Closed mid Oct. - mid April) We stock wood for the fire pit, so roast hot dogs, or make S'mores! No parties! No unregistered visitors please.

LocationValueDecor

4.96 out of 5 average rating, 442 reviews

Guest favorite

The farmhouse is set against a backdrop of lush greenery, featuring a gently sloping yard. The brick exterior is complemented by a raised stone patio adorned with small shrubs. Large windows offer a glimpse into the inviting interior, enhancing the home's warm and welcoming vibe.

Farm stay in Hermann

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.

ValueLocationBathroom

4.84 out of 5 average rating, 107 reviews

Top guest favorite

The treehouse is illuminated at night, highlighting its modern architecture nestled among trees. Warm lights glow from the windows, contrasting with the dark sky. Surrounding foliage displays vibrant orange hues, adding a serene ambiance to the outdoor setting.

Treehouse in Hermann

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.

ValueLocationCheckout

4.99 out of 5 average rating, 181 reviews

Top guest favorite

The farmhouse exterior features a two-story structure with a rusted metal roof, flanked by large trees. A welcoming front porch is highlighted by a red railing and equipped with several chairs, offering a relaxing space to enjoy the surrounding green lawn and peaceful countryside.

Farm stay in Berger

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

ValueFamilyKitchen

5.0 out of 5 average rating, 216 reviews

Guest favorite

Cabin in Bonnots Mill

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

ValueFamilyView

4.97 out of 5 average rating, 101 reviews

Top guest favorite

A single-story home with a welcoming covered porch is displayed. Greenery surrounds the house, and flower pots hang near the entrance. The porch features a pair of outdoor chairs, inviting relaxation. The light-colored exterior is complemented by a well-maintained lawn.

Home in Bowling Green

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.

LocationFamilyWalkability

4.96 out of 5 average rating, 203 reviews

Guest favorite

Apartment in Montgomery City

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.

ValueFamilyAccess

4.96 out of 5 average rating, 45 reviews

Top guest favorite

The exterior of a tiny home with a modern farmhouse design is presented, featuring a red metal roof and brown metal siding. A cozy porch area is furnished with seating, and a colorful quilt square is displayed on the wall, adding a decorative touch.

Tiny home in Fulton

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

LocationFamilyBackyard

4.99 out of 5 average rating, 308 reviews