Holiday rentals in Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor

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

1 of 1 pages1 / 1

Top guest favourite

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

4.94 out of 5 average rating, 385 reviews

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!

Guest favourite

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, 160 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 favourite

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, 126 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 favourite

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.

Flat in Sedalia

4.94 out of 5 average rating, 127 reviews

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.

Guest favourite

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

4.89 out of 5 average rating, 107 reviews

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!

Guest favourite

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

4.82 out of 5 average rating, 288 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 favourite

A charming blue cottage features a welcoming front porch with steps leading to the entryway. Lush green grass surrounds the house, complemented by landscaping and flower pots. A fence encloses the yard, providing a sense of privacy. Adjacent houses are visible in the background.

Home in Warrensburg

4.95 out of 5 average rating, 142 reviews

Colorful Cottage close to UCM

Convenient and comfortable! Our Colorful Cottage is within minutes of UCM and about 10 minutes from WAFB. We have the Cottage with all the amenities needed for a nightly, weekly, or a monthly stay. Your dogs are welcome to stay as well! Pet Policy: $30-1 dog $10-each additional Please keep dogs off of furniture at all times. Kennel if anxious or destructive when left alone. Clear waste from yard at checkout

Top guest favourite

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

4.94 out of 5 average rating, 69 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!

Top guest favourite

An open concept dining and living area is visible, featuring a large table surrounded by black chairs. The well-appointed kitchen is equipped with wooden cabinetry and ample counter space. A cozy seating area includes a light-colored sofa and a small table, with natural light illuminating the space.

Home in Hughesville

4.99 out of 5 average rating, 142 reviews

Walnut Grove Retreat

Quiet country house on a wooded lot. Entire main floor of this secluded country home, with a covered deck overlooking woods, including outdoor dining and lounge. Well appointed kitchen with open concept dining and living area. Eight miles to Sedalia, the Katy Trail and Missouri State Fairgrounds. Thirty minutes to Whiteman AFB. We welcome up to two dogs.

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, 200 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.

Top guest favourite

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

4.92 out of 5 average rating, 186 reviews

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!!

Top guest favourite

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

4.96 out of 5 average rating, 153 reviews

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.