Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Top 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, 252 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 favorite

A spacious living area is visible, featuring a cozy sofa and a patterned area rug. Natural light enters through several windows, illuminating the open layout, which includes a dining table and kitchen area in the background.

Home in Clinton

4.96 out of 5 average rating, 132 reviews

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!

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, 105 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, 109 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

An exterior view of the Stomping Ground Studio showcases a charming house with a unique stone façade and a vibrant red front door. Two front windows are framed with dark shutters, and a set of wooden stairs leads to the upper entrance. Lush greenery surrounds the entrance.

Guesthouse in Warrensburg

4.8 out of 5 average rating, 120 reviews

Stomping Ground Studio. Quaint upstairs unit

Come experience our affordable upstairs Stomping Ground Studio apartment right here in the heart of Warrensburg and the home of the University of Central Missouri Mules! Centrally located, close to the University, and downtown Warrensburg, the Stomping Ground Studio is a peaceful spot for a small getaway. Located just north of campus within walking distance to downtown Warrensburg where you will find many bars and restaurants. Enjoy our quaint, UCM themed, upstairs studio during your stay!

Guest favorite

A spacious living room features plush gray sofas arranged around a soft carpet. A TV is positioned on one side, while bright lamps provide warm lighting. Decorative wall art and a 'WELCOME' sign enhance the inviting ambiance.

Home in Warrensburg

4.98 out of 5 average rating, 175 reviews

Home Away From Home

Welcome to our charming 1920s two bedroom and one bath cottage. This cozy and well-maintained space offers a unique glimpse into the past while providing all the modern comforts you need for a comfortable stay. A king, queen and pullout queen beds give you plenty of space for rest. Off street parking for up to three vehicles and a privacy fenced back yard. Whether you're visiting for business or pleasure, our 1920s two bedroom and one bath cottage is a comfortable and nostalgic retreat.

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, 127 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, 127 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 cozy living room features a combination of comfortable seating options, including two recliners and a sofa, surrounding a wooden coffee table. A large television is positioned on a stand, while natural light filters through windows adorned with curtains, enhancing the warm atmosphere.

Home in Sedalia

4.92 out of 5 average rating, 134 reviews

Country house surrounded by woods, close to town.

Great way to get away with your family or alone. Nice country setting on asphalt road. Master bedroom includes an outside entry to a private deck and a queen bed. The 2nd bedroom comes with 2 twin beds. The 3rd bedroom has a full sized bed. The bathroom is very large with an entry from the master and the hall and includes the washer and dryer. Patio for grilling or just enjoying the scenery. Only 20 min from Truman Lake.10 minutes from Missouri State Fairgrounds.

Top guest favorite

A comfortable living area features a light-colored sofa and a patterned armchair, accentuated by natural light from large windows. A decorative mirror hangs on the wall, reflecting the cozy ambiance. Wooden flooring adds warmth to the space, complemented by floral wallpaper.

Bungalow in Knob Noster

5 out of 5 average rating, 103 reviews

Fern's Farmhouse - Minutes to WAFB and State Park

Enjoy our peaceful and relaxing country home just 1 mile from Whiteman AFB, Knob Noster State Park and Charming down town Knob Noster. Hear the birds chirping in the day and the frogs of the ponds in the evening. Surround yourself with pines, pasture, fruit trees and blackberry bushes outside and space for entertaining or family dinners inside. Built in 1940, this cute old sheep farm still holds its charm with many modern updates.

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, 132 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 .

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, 190 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.