Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Top guest favorite
Apartment in Sedalia
4.98 out of 5 average rating, 255 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, 136 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
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, 180 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, 135 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
A spacious two-story home is set on a grassy lawn, surrounded by trees and shrubs. The exterior is painted in a warm beige tone, complemented by a prominent front porch with wooden steps. A circular flower bed is arranged in the foreground, enhancing the outdoor space.
Guest suite in Sedalia
4.98 out of 5 average rating, 173 reviews

Little Lake Hideaway - Walkout Basement

Welcome to our cozy country retreat! Nestled on the lower level of our home, enjoy a private entrance to a spacious basement overlooking a scenic pond. This charming getaway features 2 bedrooms, 1 bath, an exercise room, and a family/game room for your entertainment. Step outside onto the large patio complete with outdoor dining, comfy furniture, and a grill. The kitchenette is equipped for your convenience. Relax, unwind, and immerse yourself in nature's beauty.

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, 104 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.

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, 233 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

Top guest favorite
A light-filled living area features a comfortable sectional sofa with a decorative throw pillow. A modern entertainment unit is positioned against the wall, holding a large flat-screen TV and a faux fireplace. The open kitchen can be seen in the background, showcasing white cabinetry and granite countertops.
Home in Sedalia
4.99 out of 5 average rating, 196 reviews

Haven House New Comfortable and Clean Retreat

The Haven House is great for small families, smaller wedding parties, a visit to the state fair, or couples just looking to getaway for the weekend. Also, you will be conveniently close to many popular places. Fairgrounds < 2 miles depending on gate access Downtown area 2 miles Katy Trail 1 mile or less depending on access point Heritage Ranch Event Venue 5.4 miles Hwy access Bothwell Hospital 2 miles

Guest favorite
A charming blue cottage features a welcoming front porch with steps leading to the entryway. Lush green grass surrounds the house, complemented by landscaping and flower pots. A fence encloses the yard, providing a sense of privacy. Adjacent houses are visible in the background.
Home in Warrensburg
4.96 out of 5 average rating, 101 reviews

Colorful Cottage close to UCM

Convenient and comfortable! Our Colorful Cottage is within minutes of UCM and about 10 minutes from WAFB. We have the Cottage with all the amenities needed for a nightly, weekly, or a monthly stay. Your dogs are welcome to stay as well! Pet Policy: $30-1 dog $10-each additional Please keep dogs off of furniture at all times. Kennel if anxious or destructive when left alone. Clear waste from yard at checkout

Guest favorite
A charming urban cabin is situated under a clear blue sky, featuring a light-colored exterior with a metal roof. A welcoming porch is accessible through a white front door, surrounded by greenery. Large windows allow ample natural light into the living space.
Home in Sedalia
4.91 out of 5 average rating, 107 reviews

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.

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, 191 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.

Top guest favorite
A lakeside cabin with a distinctive red exterior and metal roof is positioned next to a grassy area. A serene dock extends into the water, surrounded by open fields and a colorful sky at sunset.
Cabin in Knob Noster
4.94 out of 5 average rating, 159 reviews

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!!

Popular amenities for Windsor vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Henry County
  5. Windsor