Holiday houses in Windsor

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!

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!

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!

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.

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.

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.

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.

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!

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.

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.

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.

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!!