Vacation rentals in Montgomery City

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Top-rated vacation rentals in Montgomery City

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Guest favorite

Farm stay in Holts Summit

4.92 out of 5 average rating, 273 reviews

The Bunk House

The Bunk House is an 8 by 12 foot shed with 3-4 bunks. There is a twin sized bed across the back, a bunk sized bed on each side and a plank to pull out to accommodate a fourth person in the middle over the walkway. With this adaptation, you have an 8 by 10 foot bed. We provide foam mattresses, sheets, blankets and pillows. There is an air-conditioner and a heater. Bucket toilet behind the bunkhouse. Fire ring available. No pets. The water is from our deep well - tested, certified and delicious!

Guest favorite

Home in Bonnots Mill

4.96 out of 5 average rating, 310 reviews

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 provides abundant natural lighting. 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 parking small cars. Drive: 15-20 min to Linn for supplies / 30 min to Jeff City / 5 min to public river access.

Guest favorite

Cottage in Gasconade

4.91 out of 5 average rating, 271 reviews

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.

Top guest favorite

Home in New Florence

5 out of 5 average rating, 46 reviews

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!

Top guest favorite

Guest suite in Wright City

4.98 out of 5 average rating, 58 reviews

Private Full Kitchen Guest Suite in Quiet Location

Newly renovated apartment on the lower level of my home. You'll have privacy and room to relax or cook a meal. You'll have your own separate heating and cooling for your comfort. I want my guest to relax and enjoy...therefore, no list of chores to complete upon checkout! Located 5 miles from hwy 70 in Wright City. Approximately 13 miles from Wentzville, 20 miles from O'Fallon, 6 miles from Warrenton and 17 miles from Troy. Maximum occupancy is 2 people age ten and up (no exceptions).

Top guest favorite

Treehouse in Jonesburg

5 out of 5 average rating, 27 reviews

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.

Top guest favorite

Treehouse in Hermann

5 out of 5 average rating, 76 reviews

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.

Top guest favorite

Condo in Bowling Green

5 out of 5 average rating, 31 reviews

Cozy Townhouse Retreat

Welcome to "Cozy Townhouse Retreat," a beautifully designed new construction offering three cozy bedrooms and 2.5 baths. This modern home features high-speed internet, a convenient washer and dryer, and a cozy fire pit for those chilly evenings. Outside, enjoy an outdoor gas grill and seating area, ideal for entertaining or relaxing. With a one-car garage and off-street parking, convenience is at your doorstep. Experience comfort, style, and modern amenities all in one place!

Top guest favorite

Guest suite in Rhineland

4.97 out of 5 average rating, 232 reviews

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.

Top guest favorite

Home in Bowling Green

4.95 out of 5 average rating, 150 reviews

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.

Top guest favorite

Tiny home in Fulton

4.99 out of 5 average rating, 194 reviews

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

Guest favorite

Guest suite in Dardenne Prairie

4.89 out of 5 average rating, 292 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh