Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite

A vibrant sign displaying 'The Whistle House' is mounted on a red brick wall. The sign features distinctive typography with the words 'Morning - Noon - Night' highlighted underneath, creating a welcoming presence for visitors.

Apartment in Sedalia

4.98 out of 5 average rating, 243 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.

Guest favorite

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, 103 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 favorite

The charming stone cottage features a welcoming yellow door, flanked by two bright yellow chairs on a wooden porch. Large windows provide views of the surrounding greenery, enhancing the rustic appeal of the home. A small side table sits adjacent to the chairs.

Cabin in Edwards

4.98 out of 5 average rating, 102 reviews

Cozy getaway-Hot tub, wood stove and sunsets

Welcome to Cairn Cottage, a classic one-room, stone cottage sitting a stones throw from the Osage Arm of The Lake of the Ozarks (69MM). Relax in nature from the cabin hot tub year around. From May to September (and sometimes later) you can enjoy the Kayaks and SUPs at the lake lot. Please note that the cottage and lake lot are a short drive from each other. A boat slip is available 5/31-9/7 upon request. We always recommend travel insurance but especially encourage it during winter months

Guest favorite

A light-filled living area features a sectional sofa draped with a throw blanket. A dark coffee table rests on a contrasting area rug. A potted plant adds greenery to the space, complemented by a window allowing natural light to enter.

Apartment in Sedalia

4.84 out of 5 average rating, 169 reviews

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.

Top guest favorite

The living area showcases a warm blend of textures with a brown sofa and two gray chairs flanking a central ottoman. Sunlight filters through two windows, illuminating framed artwork on the walls, while a woven rug adds a cozy touch to the hardwood floor.

Condo in Warrensburg

4.99 out of 5 average rating, 123 reviews

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.

Top guest favorite

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

5 out of 5 average rating, 113 reviews

Beautiful Grain Bin Cabin, 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 favorite

A serene green pasture is populated by various cattle grazing peacefully. Tall grass sways gently in the breeze under the shade of large trees. The landscape offers an inviting view of the rural countryside, emphasizing the tranquil atmosphere of the farm.

Farm stay in Concordia

4.99 out of 5 average rating, 130 reviews

Sunset C B&B

Situated in the heart of Midwestern farm country, and located just minutes from I-70, Sunset C Bed & Breakfast is a working cattle ranch where owners Galen & Pam raise Akaushi (Red Wagyu) cow/calf pairs and market their own beef right on the farm. There are many opportunities for interaction with the farm animals and time to relax to watch the beautiful sunsets. Complimentary breakfast is available -visit with Pam to confirm .

Guest favorite

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.

Apartment in Windsor

4.91 out of 5 average rating, 34 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.

Guest favorite

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

4.9 out of 5 average rating, 40 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!

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, 189 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.