Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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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, 125 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!

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, 104 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, 172 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

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, 131 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 single-story home features a welcoming entrance with a black door. Decorative planters with blooming flowers line the walkway. Two white chairs and a small table enhance the outdoor seating area, while an American flag proudly hangs, adding a touch of charm to the facade.

Home in Sedalia

4.98 out of 5 average rating, 291 reviews

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.

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, 100 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, 131 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 .

Top guest favorite

A cozy bedroom features a spacious bed with striped linens and decorative pillows. A comfortable armchair and bedside tables with lamps are visible, enhancing the room's functionality. Natural light enters through small windows, adding brightness to the neutral color palette.

Home in Appleton City

4.97 out of 5 average rating, 230 reviews

Tiny Cottage

Escape the big city hustle and bustle for a cozy tiny home with eclectic style in our safe small town of Appleton City. Enjoy the fresh air and open fields. Off street parking. Perfect for a couples get away. There's coffee, toaster, basic kitchen essentials, mini fridge with ice cube trays, lawn chairs for the front porch where you can enjoy your coffee in the morning shade in our quiet little escape. No pets

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, 41 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.