Vacation rentals in Clarksville

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Top-rated vacation rentals in Clarksville

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

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Top guest favourite
The cabin's exterior is viewed from a grassy area, showcasing a covered porch with steps leading up to the entrance. Two white doors are framed by light-colored walls, while a red wreath adds a touch of color. The natural surroundings feature trees in the background.
Cabin in Winchester
4.96 out of 5 average rating, 188 reviews

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.

Top guest favourite
A cozy cabin is nestled among tall trees, featuring a welcoming front porch and a green door. The surrounding lawn is well-kept, with open fields visible in the distance, creating a peaceful and serene setting.
Guesthouse in Jerseyville
4.96 out of 5 average rating, 184 reviews

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.

Guest favourite
The kitchen features white cabinetry and modern black appliances. A spacious countertop offers seating at two metal stools. Natural light filters through the windows, illuminating the wooden flooring and classic tile backsplash.
Home in Hannibal
4.95 out of 5 average rating, 199 reviews

Little House in the Hollow

Enjoy a private peaceful setting that is Conveniently located. Large fenced in yard for the kids and/or pets. Also has a 4 person hotub which is available year-round. The house is fully stocked for convenience. The house also has covered parking, outdoor fire pit, BBQ grill a play place for the kids and more. You will be within walking distance of 2 National Landmarks (Mark Twain Cave, Cameron Cave) as well as our Winery and Giftshop. Located just two miles from Hannibal's Historic District.

Top guest favourite
Condo in Bowling Green
5 out of 5 average rating, 60 reviews

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

Guest favourite
Home in Bowling Green
4.96 out of 5 average rating, 215 reviews

Peaceful Country Cottage

Traveling for work or pleasure? Enjoy a peaceful country view while relaxing on the front porch. This home sits on 14 acres, just off US Highway 61. Guests will see deer roaming in the yard early morning and at night. This rental accommodates families traveling with children or the couple seeking a quiet retreat. Stay here while you visit family and friends in the area. It is a short drive to Vandalia, Louisiana, Hannibal or Mark Twain Lake. (40 Min). About one hour from St. Louis.

Top guest favourite
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
4.99 out of 5 average rating, 144 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 favourite
A cozy dining area is highlighted by a wooden table surrounded by four chairs. Antique stained glass windows illuminate the space with soft colors. A small kitchen area is visible in the background, featuring modern appliances and bright cabinetry.
Cabin in Jacksonville
4.97 out of 5 average rating, 397 reviews

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

Top guest favourite
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
4.96 out of 5 average rating, 178 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.

Guest favourite
A river cabin sits elevated on stilts, surrounded by lush greenery, with a spacious deck offering views of the Mississippi River. A concrete patio leads to the water's edge, where a wooden dock allows for easy access. The peaceful setting is enhanced by mature trees in the background.
Treehouse in Annada
4.89 out of 5 average rating, 80 reviews

“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!

Guest favourite
A cozy living area features a black sofa with decorative pillows and a wooden coffee table at its center. Natural light streams through two windows, illuminating the neutral tones and textured decor. A small accent chair and a patterned rug complete the inviting space.
Loft in Winchester
4.94 out of 5 average rating, 166 reviews

The Bike Flat

Visit historic Winchester and explore what our quaint community has to offer! This stylish place to stay is perfect for a quiet getaway and can accommodate groups thanks to its ample space. You can bring the family or plan a getaway with friends. The flat is located above a newly opened bicycle and coffee shop that also offers craft beers and wine. We hope you will consider choosing our rural accommodations for a trendy and relaxing experience!

Top guest favourite
A modern studio cabin is elevated on pillars, surrounded by lush greenery. The exterior features dark wood siding and multiple windows, allowing natural light to illuminate the interior. A deck is visible, indicating outdoor space for relaxation.
Farm stay in Grafton
4.97 out of 5 average rating, 349 reviews

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.

Top guest favourite
A wooden dock extends over a calm lake, reflecting the surrounding trees and cloudy sky. A solitary chair is placed at the end of the dock, offering a peaceful spot to admire the serene waters.
Cottage in Montgomery City
4.99 out of 5 average rating, 403 reviews

Small private country home with lake, spa, firepit

Country setting, 3/4 mile from town, house on 20 acres, lake, woods in back round, firepit, spa and BBQ area under pergola. 10 minutes from I-70. 25 minutes to Warrenton, 30 minutes from Hermann, Mo. 50 minutes to Columbia and Wentzville, MO. Great place for a staycation, traveling, work from home, or a vacation. Child and pet friendly with lots of running room.

Popular amenities for Clarksville vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Pike County
  5. Clarksville