Vacation rentals in Clarksville

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.

Container Home GREAT Countryside Views COZY Stay

Singing Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

Cozy Townhouse Retreat

Welcome to "Cozy Townhouse Retreat," a beautifully designed new construction multi level townhome offering 3 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

Nature Escape-170 Country Acres

Unwind at this one-of-a-kind cabin nestled on 170 private acres of rolling countryside. Perfect for families, couples, or small groups, this retreat blends rustic charm with modern comfort. Grill dinner on the deck, and gather around the firepit under a sky full of stars. Inside, you’ll find a cozy open layout with a fully equipped kitchen, inviting living spaces, and comfortable bedrooms with warm cabin décor. Large windows bring the outdoors in, offering views of the woods and water.

Historic Loft on Adams

Charming updated loft-style studio in the heart of quaint downtown Pittsfield. Located within walking distance of restaurants, the historic courthouse, and local bars. This private apartment is perfect for weekend getaways, staycations, or even a cozy home base to work from remotely. The view of our Pike County Courthouse from any window is gorgeous and the historic building has so much character, all in a convenient, central location. This second floor loft is completely private.

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.

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.

“Exclusive” River Cabin on Stilts (3 bedroom)

Your Perfect Riverfront Getaway Awaits! Nestled in a laid-back river cabin community, this charming cabin offers stunning views of the mighty Mississippi River. Whether you're into fishing or simply soaking up nature, the abundant wildlife and serene setting make it the ideal place to unwind. This cabin, elevated on stilts to protect from seasonal flooding, features three spacious bedrooms, one bath, and recent updates. Don’t miss out – book your escape today!

The Yellow Rose Historic Home

This cozy home is 8 blocks to the Mississippi. Beautiful overlooks, nice restaurants, historic homes. A short drive to Two Rivers Marina, the SLU Lay Center Sculpture Park, Hopewell Winery, Ted Shanks Conservation Area, Clarksville Apple Shed. 30 min. to Hannibal, MO - home of Mark Twain. 45 min. to Mark Twain Lake. 90 min. to St Louis. Plenty of sight-seeing, hunting, fishing, boating in the area. Fur babies are welcome.

Pere Ridge Tree Escape with private hot tub

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a 10 minute drive to Grafton.

Dairy Farm Stay • Fresh Eggs & Milk • Peaceful 2BR

Escape to a quiet dairy farm where you can wake up to cows, calves, fresh eggs, and peaceful country views. Our cozy 2-bedroom farmhouse sleeps up to 7 and offers full kitchen, WiFi, and plenty of trailer parking. Perfect for families, hunters, workers, or anyone needing a quiet getaway Easy day trips to Bowling Green, Wentzville, or St. Louis