Holiday rentals 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 Dog House! Downtown Burg 2 bedrooms

Come, sit, stay in a brand new two bedroom 1 bath apartment in downtown Warrensburg-Home of Man's Best Friend! Located on the courthouse square the open concept living room and kitchen have fabulous views of downtown and the Old Drum monument. Features 2 queen beds, outdoor patio, off street parking, full bathroom and laundry room. Walk to our famous "Pine St." for food, fun and drinks and enjoy all our beautiful downtown has to offer. 4 blocks north of UCM campus and Walton Stadium.

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.

The Meyer House

Be our Guest! Adorable 1 Bedroom home all to yourself. Relax in this freshly decorated home. We have Wifi Alexa Smart TVs in living room and bedroom. Kitchen is fully equipped with everything you need and more. We have a barbeque grill and patio set. Washer and Dryer for you to use. Private/ public parking in front/back of house that is protected with a ring doorbell. We would love for you to stay with us at The Meyer House. Thanks Christene and Billy Meyer.

Private cabin close to the lake

Come stay in our guest bunkhouse! Situated in the middle of 40 acres of beautiful land. We have a pond, and several walking trails on the property. We are only 5 minutes from Truman lake and Lake of the Ozarks! Plenty of parking for your boat or vehicle. This house has 1 queen bed, 1 full size bed, and 2 twin beds. Kitchen has coffee maker (coffee & supplies included), small refrigerator, and microwave. TV with Dish channels. We love fisherman, so come see us!

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.

Urban Cabin

Keep it simple at this peaceful and centrally-located Urban Cabin. Pet friendly with a fully fenced-in back yard and outdoor dog house. This cozy home is located just a few blocks from Centennial Park and the hospital. We're also a short drive to the Missouri State Fairgrounds, Downtown Sedalia, and the Katy Trail.

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.

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!

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.