Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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

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Top guest favourite
Flat in Sedalia
4.99 out of 5 average rating, 282 reviews

The Whistle House

Be Our Guest at The Whistle House our building was built in 1906. It was home to Whistle Soda Bottling Company. We have renovated the apartment in the building. Relax and Enjoy! We have WIFI, 2 Smart TV's among everything else you could need. Katy depot is .08 miles for Katy trail riders. We are close to downtown, Ozark Coffee is .05 miles, Lamy building .03 miles which has Bistro No. 5 & Bar, Foundry 324 Event Center. We would love for you to stay with us. Billy & Christene Meyer.

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, 371 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!

Top guest favourite
A cozy living room features a gray upholstered armchair beside a large area rug. A brick fireplace with a glass front is centered beneath a flat-screen TV. Natural light enters through two windows with sheer curtains, creating a warm ambiance. Decorative plants and a wooden welcome sign add charm.
Home in Warrensburg
4.97 out of 5 average rating, 412 reviews

Downtown Retreat with large privacy fenced yard

This updated downtown retreat has two bedrooms, 1 bath, kitchen, living room, dining room and laundry. Off street parking is behind the house. This property has a large fenced in yard with deck and firepit. Majority of the time you can catch a nice breeze in the backyard while you relax. In the winter you can enjoy the gas fireplace in the living room and stay warm. Downtown is just walking distance way with historic sites and restaurants, coffee shops and shopping.

Top guest favourite
A welcoming exterior of a cabin features a covered porch with two blue chairs and decorative greenery. Double doors with a wreath invite guests inside, while a grassy area extends beside the gravel driveway. A garage door is visible on the side.
Cabin in Warsaw
4.97 out of 5 average rating, 105 reviews

Countryside Cabin by the Lake

This spacious cabin has 1 bedroom with a comfortable, king sized bed, a queen sized hide a bed couch in living room, and a well equipped kitchen. The outside sitting area is a peaceful oasis with the view of the cattle and horse farm. An outside outlet is available for charging your boat. Bike, walking trails, and a marina are all within 1. 4 miles. Downtown shopping area is 5 minutes away. Roku and wifi are available.

Top guest favourite
The entrance features a welcoming white door with a glass panel, flanked by two large windows on either side. Potted plants are placed in decorative black bases, and a small wooden bench is positioned beside the entrance, enhancing a home-like appeal.
Place to stay in Lincoln
5 out of 5 average rating, 61 reviews

Restored Building in Downtown Lincoln!

Do you need to get away from it all? Come to Fisher's Hide-a-Way and find a little rest and relaxation! Located in a lovingly restored building on historic Main Street in quaint Lincoln, MO where the down-town is being renovated one building at a time. Loaded with amenities such as luxury bedding and extra soft and fluffy towels, this vacation rental has everything you are looking for in that much needed break!

Guest favourite
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.
Flat in Windsor
4.93 out of 5 average rating, 43 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.

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
4.93 out of 5 average rating, 59 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
The motor coach is positioned on a gravel area, showcasing a sleek exterior with a blend of earth tones. A slide-out section expands the living space, while large windows offer natural light. Trees are visible in the background, providing a green contrast to the vehicle.
Camper van/Motorhome in Windsor
5 out of 5 average rating, 22 reviews

Da Bus @ Red Barn Luxury Motor Coach

Only a hop skip and jump from the KATY and Rock Island Trails. Da Bus is a 2003 Tiffin Class A Luxury Motor Coach. The Master Bedroom has a Queen Bed, The couch in the living area folds out to a Full size bed. The kitchen has a large refrigerator and freezer, double sink, new faucet, propane stove top, Microwave/convection oven. The large shower has a new faucet and hand wand.

Superhost
The Hideaway Cabin is set amidst leafless trees, showcasing its well-maintained exterior with a sloped roof and a welcoming front porch. A gravel driveway leads up to the cabin, while a wooden sign labeled 'The Hideaway' marks the entrance to the property.
Home in Lincoln
4.95 out of 5 average rating, 21 reviews

The Hideaway

Escape to the Hideaway Cabin in the Ozarks, just a stone's throw away from Lake of the Ozarks! Whether you're planning a relaxing vacation, a hunting expedition, or a fishing trip, this cabin is the place to be. The nearsest town is only 10 minutes away, with anything you might need. Including a mom and pop diner and a cozy coffee shop if you're into that kind of thing.

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, 194 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.

Guest favourite
A charming cottage is nestled within a serene countryside setting, illuminated by soft outdoor lighting. Large windows reflect warm interior light, while a lush lawn and mature trees provide a peaceful backdrop. The walkway is lined with subtle lighting, enhancing the inviting ambiance.
Home in Calhoun
4.73 out of 5 average rating, 110 reviews

Tropical Country Cottage

Relax with the whole family at this peaceful place to stay. Access to 3 acres of countryside property with plenty of room to enjoy. Less than a mile from the Katy Trail; perfect for riding bikes and exploring. Also near Truman Lake; great for fishing and relaxing by the water!

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
4.94 out of 5 average rating, 177 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