Some info is shown in its original language. Translate

Holiday houses 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.

%{current} / %{total}1 / 1
Guest favourite
A welcoming cabin exterior is framed by lush greenery. A red metal roof contrasts with the earthy tones of the cedar siding. Colorful directional signs mark nearby attractions, while a gravel driveway leads up to the inviting porch area with chairs for relaxation.
Cabin in Warsaw
4.92 out of 5 average rating, 111 reviews

NAMA Stays - Cozy Cabin

This charming cabin features handcrafted cedar walls and bar top, ideal for family getaways. It accommodates up to 6 adults with a futon in the living room, twin bunk bed over a standard mattress in one bedroom, and a queen-size master bedroom. Enjoy ample parking, outdoor seating options, a fish cleaning station with a restaurant-quality cutting board, fire pit, firestick TV, and numerous games. Located a short drive from Warsaw, Truman Lake, and Lake of the Ozarks, accessible via Drake Harbor.

Top Guest favourite
Cabin in Edwards
4.99 out of 5 average rating, 138 reviews

Hot tub, golf cart, kayaks/SUP with lake access!

✨Hot Tub+Golf Cart+Kayaks |Quiet Lake Escape Cairn Cottage is a cozy, vintage, one room stone cottage tucked into nature above the Osage Arm (69MM). Come slow down and enjoy the quiet side of the lake. Hot tub year-round, golf cart to the dock, and kayaks in season. A complimentary breakfast casserole, plus coffee and snacks, make mornings simple and relaxed. Not coming in summer? Check out our amenities slide that shares which amenities are available when. Reconnection is a reservation away!

Guest favourite
A spacious bed is positioned near large windows, offering a scenic view of serene woodlands blanketed in snow. Soft gray bedding contrasts with the vibrant greenery outside, which is visible through the clear glass panes, creating a tranquil atmosphere.
Home in Warsaw
4.94 out of 5 average rating, 362 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, the historic "Hallmark town" of Warsaw is minutes away, and a 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!

Top Guest favourite
The exterior of the Grain Bin Cabin is showcased beside a tranquil pond, reflecting the cabin's metallic structure. Adirondack chairs surround a firepit on the grass, with picnic tables positioned nearby, creating an inviting outdoor space.
Cabin in Versailles
4.99 out of 5 average rating, 164 reviews

The Highland GrainBin, Highland Cows, Firepit

Welcome to our charming boho-inspired Grain Bin Cabin, the Highland is ideal for 2-3 adults or 2 adults and 2 smaller children. Upstairs, you'll find a comfortable king bed in the loft, while downstairs features a cozy futon in the main living space. The full kitchen is equipped with everything you need. Full Bath with a walk-in shower downstairs. Experience a serene countryside getaway with breathtaking sunsets and peaceful surroundings, just moments away from Versailles.

Top Guest favourite
Two blue mugs are placed on a glass-topped table overlooking the serene lake. The calm water reflects the surrounding tree-covered hills, creating a peaceful setting. Soft morning light illuminates the scene, enhancing the tranquil atmosphere of this lakeside retreat.
Home in Edwards
4.97 out of 5 average rating, 279 reviews

Rippling Point Lakefront House

Secluded at the end of a private drive on the quiet end of the Lake of the Ozarks, our lake home offers recreation, relaxation, and fishing opportunities. The house is on the water at the 67MM of the lake and features 300 feet of private shoreline. A deck that overhangs the water is just a few steps from a patio equipped with a propane/charcoal grill and outdoor cooking area. Two kayaks are included to explore the shoreline and its wildlife. An inviting hot tub beckons.

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, 267 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.

Top 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
4.96 out of 5 average rating, 123 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

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
4.92 out of 5 average rating, 50 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, 124 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.

Top Guest favourite
The cottage exterior is shown, featuring a green façade with white trim. A welcoming porch extends from the front, adorned with a wooden pergola. A grassy area surrounds the home, with trees lining the background, creating a serene atmosphere.
Home in Lone Jack
4.99 out of 5 average rating, 238 reviews

Rock Valley Ranch Cottage on 15 acres, sleeps 4

Enjoy a peaceful stay at our newly remodeled cottage near Lone Jack. A beautiful property on 15 acres, overlooking a pond, roaming horses and an array of wildlife. Located just 15 minutes east of Lee's Summit and 35 minutes from the Plaza. Join us for a weekend away or stay all week with friends and family at Rock Valley Ranch!

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, 193 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
4.93 out of 5 average rating, 168 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!!

Popular amenities for Windsor holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Henry County
  5. Windsor