Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

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Top guest favorite

A spacious master bedroom is shown, featuring a bed positioned near large windows that provide expansive views of the surrounding landscape. Soft carpeting covers the floor, and natural light fills the room. A small area is visible to the left, suggesting additional amenities.

Home in Warsaw

The Overlook

Adventure awaits! Enjoy the best sunsets and night skies from high above the shores of Truman Lake. An unforgettable way to unwind! Perfect for romantic getaways, thrill seekers, and tourists alike. Protected forests surround the neighborhood and the historic "Hallmark town" of Warsaw is minutes away. A modern marina is just down the road. Great opportunities for relaxation and recreation abound with memorable times sure to be had! Ask about our romance/birthday packages and pet friendly stays!

4.94 out of 5 average rating, 387 reviews

Guest favorite

A spacious living area is furnished with a light-colored sectional sofa and a dark coffee table, contrasting against the tiled floor. A flat-screen TV is mounted on the wall, alongside a modern stand. A dining table and chairs are positioned near a window, allowing natural light to enter.

Apartment in Sedalia

Minimalist centrally located apartment in Sedalia

Whether you are here for the Fair, passing thru on the trail/highway, or are a contract worker, come stay and rest at our place. We are conveniently located 0.5 miles from the entrance to the fair as well as the Katy trail. We have a cozy 2 bedroom 1.5 bath unit with a 70” tv that can fit 4 individuals comfortably. Hungry? We are located 1 block away from Sonic, Subway, two Mexican and a Chinese restaurants. McDonald’s, Burger-King, TacoBell, Dominoes and Pizza Hut are less than a mile away.

4.95 out of 5 average rating, 128 reviews

Guest favorite

A spacious living area features a round wooden dining table with four black chairs. A green sofa is positioned near a large television, with a small decorative tree and coffee table visible. Soft lighting from a nearby window enhances the inviting space.

Home in Warrensburg

The Den at Cave Hollow

A Cozy Retreat in Warrensburg, Mo! Nestled at the edge of Cave Hollow Park, The Den at Cave Hollow is a perfect getaway. Whether exploring the caves, enjoying downtown, or UCM, our location is convenient. Start your day with a hike through the trails of Cave Hollow Park. We’re also just minutes from the heart of downtown Warrensburg and Whiteman AFB. Come experience the best of Warrensburg from The Den at Cave Hollow! We look forward to hosting you. Book now and start your adventure!

4.95 out of 5 average rating, 121 reviews

Guest favorite

An A-frame house is nestled among lush greenery, featuring a striking blue exterior. The front has large triangular windows that allow natural light to fill the interior. A spacious wooden deck with railings provides outdoor seating, inviting relaxation in a serene environment.

Home in Clinton

A-Frame Escape

Escape the weekly grind and relax at our peaceful A-Frame. Nestled in nature but close to the essentials, you'll love it here so much you won't want to leave. This is our family lake house. Surrounded by tranquil nature, you will be at peace. The home is centrally located near several marinas for great fishing and boating, with plenty of parking for boats and trailers. Relax on the large deck or unwind in the hot tub. Come stay at our lake house and become part of our lake family!

4.89 out of 5 average rating, 108 reviews

Guest favorite

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

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.

4.82 out of 5 average rating, 290 reviews

Top 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

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!

4.95 out of 5 average rating, 74 reviews

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

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.

4.88 out of 5 average rating, 201 reviews

Guest favorite

The open living area features comfortable leather seating arranged around a wooden coffee table, complemented by a warm rug. A fireplace with a modern design is visible, with a TV mounted above it. The kitchen, with its light cabinetry and dark countertops, is open for easy entertaining.

Home in Sedalia

Aunt B's House *No Cleaning Fee*

Hello we are the new owners of this beautiful 3 Bed 2 Bath House that has everything you could need for your stay. Talk about the best location in town being less than 1 mile from all major amenities, MO State Fair Grounds, and more. We have no cleaning fee and a stress free check out!

4.94 out of 5 average rating, 189 reviews

Top guest favorite

A lakeside cabin with a distinctive red exterior and metal roof is positioned next to a grassy area. A serene dock extends into the water, surrounded by open fields and a colorful sky at sunset.

Cabin in Knob Noster

Cabin by the lake

Sit back, relax and enjoy your stay at this unique lakeside cabin!! Feel free to enjoy catch and release fishing and the peaceful setting on the dock! We hope you have a wonderful stay and please let us know if there’s anything we can do to improve your experience!!

4.92 out of 5 average rating, 188 reviews

Top guest favorite

The exterior of a rustic structure features a wooden porch with a pergola, providing shaded space for seating. A bright red door is positioned centrally, with a grill and potted plant nearby. The surrounding area is open with bare trees and grassy land.

Cabin in Lincoln

The Carolyn Cabin

This is a peaceful place to stay in a country setting. Centrally located near both Truman Lake and the Lake of the Ozarks for all of your family fun! When you are not enjoying the water, you can be grilling on our cozy outdoor patio and meet our farm animals.

4.96 out of 5 average rating, 156 reviews

Top guest favorite

A compact cabin is situated on a grassy area, surrounded by lush greenery. A seating arrangement with a round table and chairs is visible in front of the cabin. A fire pit is positioned nearby on the gravel ground, inviting outdoor gatherings.

Cabin in Windsor

Trailside camping/sleeping cabin

Bunk style sleeping cabin located in Windsor MO at the junction of the Katy and Rock Island trails. Includes separate restroom/ shower facility and secure bike storage area. Cabin has heater and a/c as well as outlets to charge electronic devices.

5.0 out of 5 average rating, 16 reviews

Top guest favorite

A wooden glider sits on the porch of a cabin, accompanied by a potted flower. Natural light filters through a window with wooden shutters, enhancing the cabin's rustic appeal. A door with a simple design is visible, inviting guests to enjoy the peaceful surroundings.

Cabin in Windsor

Kim's Cabins #1 - Modern tiny house cabin sleeps 4

Kim's Cabins offers 4 modern cabins in a peaceful setting close to the Katy Trail in friendly Windsor, MO. Located close to shopping, restaurants, wildlife and Amish community. Whether bike riding, hiking, or a getaway - come enjoy the quiet life

4.99 out of 5 average rating, 162 reviews