Vacation rentals in Henry County

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Top-rated vacation rentals in Henry County

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Top guest favorite

A spacious living area is visible, featuring a cozy sofa and a patterned area rug. Natural light enters through several windows, illuminating the open layout, which includes a dining table and kitchen area in the background.

Home in Clinton

4.96 out of 5 average rating, 132 reviews

The Orchard House by Katy Trail

Dubbed the Orchard house since being on Orchard street. This newly renovated stand alone home on a quiet dead end road is just what the doctor ordered. Located just 2 miles to the start of the historic Katy Trail makes this a great spot. Also, we are only minutes away from Truman Lake which boasts some of the best crappie and spoonbill fishing around. A dedicated shed with lock is provided at the back of the home for bike storage. A short walk to the historic square with shopping + eateries!

Top guest favorite

The entrance to the home features a wooden deck with steps leading up to the front door, framed by two windows with green shutters. A metal sculpture of a child fishing stands beside the steps, with a decorative rocky landscape and lush plants below.

Home in Deepwater

4.96 out of 5 average rating, 112 reviews

A Cozy Getaway

Minutes away from Harry S. Truman Dam & Reservoir & the upper end of the Lake of the Ozarks. The lake is a popular fishing destination for crappie, largemouth bass, hybrid stripers, catfish, as well as some of the Nation's finest snagging for spoonbill paddlefish. The surrounding area (110,000 acres) provides plentiful & diverse opportunities, including hiking, horseback riding, golfing, biking, bonfires, bird watching, off-road vehicle adventures, & some of the best hunting in the country.

Guest favorite

A tranquil pond reflects the vibrant autumn foliage surrounding it, with a serene house nearby nestled among mature trees. The still water adds to the peaceful atmosphere, enhanced by the clear blue sky above.

Farm stay in Clinton

4.83 out of 5 average rating, 24 reviews

AutumnSerenity@ BoulderHollow Hideaway

Escape to peace and quiet in every season at our secluded woodland retreat. Nestled at the end of a private road, our property offers the perfect setting for a romantic getaway, remote work escape, or a home base for exploring nearby Truman Lake. Enjoy views of our tranquil backyard pond, seasonal above-ground pool, lush gardens, and the surrounding creek valley. Whether you’re here to reconnect with nature or to head out on the lake, Boulder Hollow Hideaway is your perfect place to getaway.

Top guest favorite

A gravel driveway leads through a lush green field, bordered by grassy areas on either side. In the distance, a farmhouse is visible, surrounded by trees under a partly cloudy sky. The natural landscape conveys a sense of open space and tranquility.

Farm stay in Deepwater

4.95 out of 5 average rating, 55 reviews

"Private" House -30 acres {Bucksaw Marina-Truman}

Have a peaceful and relaxing stay in a Farm house ! 7 minutes away from Bucksaw Marina 18 minutes to Long Shoals ! Huge Deck to enjoy grilling and chilling!15 minutes from Clinton , Missouri to get groceries or to dine out. 1 bedroom with 2 king size beds and a bunk room with 2 full size beds and 2 twins on top. Plenty of parking . 1 bathroom with a shower. Laundry room with a washer and dryer. Pets are welcome also! Small pond to let kids fish! Trails on property to walk or enjoy wildlife!

Superhost

A spacious log cabin is set among lush green trees, featuring a large wraparound deck supported by sturdy wooden posts. The exterior showcases a well-maintained wooden façade, allowing natural light to accentuate the windows, which provide views of the surrounding woodland.

Cabin in Warsaw

4.76 out of 5 average rating, 71 reviews

Luxury Log Cabin - Truman Lake

Tir Na Nog – “Forever Young” A Rustic Retreat Near Truman Lake Welcome to our cozy log cabin, tucked away in the peaceful woods—where time slows down, screens fade away, and you reconnect with life. Named after the Irish legend meaning "Forever Young," it restores & lifts spirits. Whether you’re a hunter, angler, nature lover, or just need a break from everyday life, this is where memories are made—around the campfire, under starry skies, or curled up inside as the wood stove crackles :)

Top guest favorite

A rustic cabin with a dark wood exterior is surrounded by greenery. The front porch features a railing and planters with hanging flowers. Large windows allow natural light inside, while trees provide shade and a peaceful atmosphere.

Cabin in Deepwater

5 out of 5 average rating, 19 reviews

Sweet Peace Cabin

Completely renovated beautiful cabin on 3 peaceful acres. Spacious 2 queen bedrooms sleeps 4 adults, 2 full baths with an upstairs loft that sleeps another 3/4 people. Full covered decks on both front and back with firepit and grill to cook your day's catch on. Neighborhood is secured by video cameras, so perfect place to relax with the family safely. Cabin is within minutes of Truman State Park and Long Shoals marina. Close to Warsaw, shopping, food and fun.

Guest favorite

A modern pavilion is illuminated by string lights, surrounded by a wooden deck and a gravel path. Tables and chairs are positioned on the deck, with large windows revealing a warm interior. A ladder leans against the structure, and trees provide dappled shade.

Home in Clinton

4.88 out of 5 average rating, 26 reviews

The Farmhouse at Truman Lake

Make memories at this unique 100 year old modern farmhouse on 20 acres. Located right off highway 7 (bit noisy) between Clinton and Warsaw. Golfcarts welcome, no off road...designated pathways only. Outdoor smoking room, pavilion (almost ready), fish cleaning, smoker, propane & charcoal grills available. Enjoy the goats “Oliver” and “Wilma” as well as our friendly chickens and ducks. Fun family vacation. Property shared w/ 3 RV pads. Minutes from water.

Guest favorite

Colorful flowers are arranged in a garden bed, featuring various blooms, including yellow and purple irises, surrounded by lush green grass. The background shows a cabin with wooden siding, framed by tall trees and a clear sky.

Home in Clinton

4.91 out of 5 average rating, 35 reviews

Cozy Cabin by Bucksaw Marina, Truman Lake

Your family will be comfortable and close to the lake when you stay at this 3 bedroom, 2 bathroom cabin. Ask us about our stocked private pond and we can get you access. It’s only a quarter mile away from the property! Also, there’s a small event center on the property that can be rented daily. Next to this house is also an RV hookup and water for extra guests. Enjoy the barbecue grill and two large walkout decks as you bask in the evening sunset.

Superhost

A serene gravel path winds through a wooded area, flanked by tall trees adorned with golden and orange autumn leaves. Soft sunlight filters through the branches, casting gentle shadows on the ground, creating a peaceful setting for a nature walk.

Cabin in Blairstown

4.81 out of 5 average rating, 259 reviews

Honey Creek Hideaway at Back Country Camp

Escape to this quiet, seemingly remote country getaway nestled down a peaceful, tree-canopied lane. Relax and unwind amid big woods, creeks, woodland trails, complete with a very large strip pit lake, and smaller lake just mere feet from your private cabin. Use our large covered dock, kayaks, paddle boat, canoe and explore all this huge waterscape and land have to offer. All manner of Missouri wildlife reside here.

Guest favorite

The image depicts a single-story brick apartment building with a white metal roof. Large windows adorned with light curtains are visible, complemented by framed artwork featuring bicycles on the walls. A well-maintained grassy area is present in front, enhancing the welcoming appearance.

Apartment in Windsor

4.91 out of 5 average rating, 35 reviews

Haven Hitch Hideaway

Cozy Windsor studio ideal overnights or a week, but also great for traveling nurses, mid-term stays, or insurance housing. Features a queen bed, twin hide-a-bed, Roku TV, full kitchen, and separate laundry room with washer/dryer. Secure indoor bike parking. Easy access to Katy & Rock Island Trails. A block from downtown with off-street parking. Quiet, clean, and perfect for extended stays or weekend getaways.

Guest favorite

A single-story home with a blue exterior and a covered front porch is shown. The porch features a light wooden railing, and the entrance door is framed by two windows. A clear sky and surrounding trees are visible, indicating a serene outdoor environment.

Home in Windsor

4.91 out of 5 average rating, 44 reviews

Windsor Blueberry

Freshly renovated 2BR in central Windsor—perfect for Katy Trail trips or nearby weddings (The Moment & Evelyn Valley Ranch)! Sleeps 4 with comfy beds, WiFi, Smart TV, full kitchen, coffee station, and laundry. Relax on the deck with bike ramp + indoor storage. Quiet neighborhood close to trailheads. Pet-friendly (2 dogs under 25lbs, $25/night). Bathroom essentials included for a cozy, carefree stay!

Superhost

The charming exterior of the house showcases a front porch with a wicker chair, welcoming guests. Fresh green grass surrounds the home, while mature trees offer shade. The roof features architectural shingles, and the door is framed by a decorative design.

Home in Windsor

4.88 out of 5 average rating, 190 reviews

The Broken Spoke

"The Broken Spoke" nightly rental sits on just over a quiet acre of land only steps from the Katy Trail and minutes from local restaurants and shopping. We can accommodate up to six in the house, we have additional camping space available for larger groups upon request, as well as extended stay rates.