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 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!

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.

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!

Lovely 2 bedroom place with free parking

Whether you are here for the State Fair, passing thru on the trail or the highway come stay and rest at our place. We are conveniently located 0.5 miles from the east entrance to the fair as well as 0.5 miles from the Katy trail. We have a cozy two bedroom unit that can fit 4 adults and a kid on the couch. Hungry? We are located one block away from Sonic, Subway, two Mexican and a Chinese restaurant. McDonald’s, Burger-King, TacoBell, Dominoes and Pizza Hut are less than a mile away.

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.

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!

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!!

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.