Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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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
4.97 out of 5 average rating, 146 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 exterior of a two-story house is depicted, featuring a gabled roof and a unique cupola. A spacious porch is visible at the front, with a bench and large triangular windows on either side. Surrounding greenery, including blooming trees, enhances the setting.
Home in Warsaw
4.98 out of 5 average rating, 210 reviews

The Citadel - Close to the Water and Warsaw

The Citadel is a pretty little place, modern with vintage cottage appeal right off Hwy 7 by the mile-long bridge leading into Warsaw. This 2 story, 2 bedroom, 2 full bath home (showers only) offers a well equipped kitchen, dining, living & sitting room w/Roku tv and tv w/dvd player, wifi, room to work, and outdoor seating. Large parking area. Close to swim beaches, the park at Drake Harbor for walking/boating/fishing, flea markets, antique shops, restaurants and the Overlook. No washer/dryer

Guest favorite
A spacious living area is furnished with a light-colored sectional sofa and a dark coffee table, contrasting against the tiled floor. A flat-screen TV is mounted on the wall, alongside a modern stand. A dining table and chairs are positioned near a window, allowing natural light to enter.
Apartment in Sedalia
4.93 out of 5 average rating, 106 reviews

Minimalist centrally located apartment in Sedalia

Whether you are here for the Fair, passing thru on the trail/highway, or are a contract worker, come stay and rest at our place. We are conveniently located 0.5 miles from the entrance to the fair as well as the Katy trail. We have a cozy 2 bedroom 1.5 bath unit with a 70” tv that can fit 4 individuals comfortably. Hungry? We are located 1 block away from Sonic, Subway, two Mexican and a Chinese restaurants. McDonald’s, Burger-King, TacoBell, Dominoes and Pizza Hut are less than a mile away.

Guest favorite
A spacious bed is positioned near large windows, offering a scenic view of serene woodlands blanketed in snow. Soft gray bedding contrasts with the vibrant greenery outside, which is visible through the clear glass panes, creating a tranquil atmosphere.
Home in Warsaw
4.94 out of 5 average rating, 357 reviews

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, the historic "Hallmark town" of Warsaw is minutes away, and a 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!

Guest favorite
Home in Climax Springs
4.94 out of 5 average rating, 109 reviews

Family fun! Secluded cove and private slip!

Come stay at the Hawks Nest! Great location with MANY different outdoor areas to enjoy. Our house is set up wonderfully for families. Quiet secluded cove with buoyed off swim area and an abundance of wild life. Boat slip, Lily pad, kayaks and a paddle boat included for use with rental. Life jackets for all sizes. Great fishing, poles provided. Open main floor and plenty of comfortable sleeping. Located at the 48.5 MM. Close to Red Fox, Big Dicks and just a boat ride from many others!

Top guest favorite
Two blue mugs are placed on a glass-topped table overlooking the serene lake. The calm water reflects the surrounding tree-covered hills, creating a peaceful setting. Soft morning light illuminates the scene, enhancing the tranquil atmosphere of this lakeside retreat.
Home in Edwards
4.97 out of 5 average rating, 276 reviews

Rippling Point Lakefront House

Secluded at the end of a private drive on the quiet end of the Lake of the Ozarks, our lake home offers recreation, relaxation, and fishing opportunities. The house is on the water at the 67MM of the lake and features 300 feet of private shoreline. A deck that overhangs the water is just a few steps from a patio equipped with a propane/charcoal grill and outdoor cooking area. Two kayaks are included to explore the shoreline and its wildlife. An inviting hot tub beckons.

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, 309 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 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, 179 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, 106 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 serene gravel path winds through a wooded area, flanked by tall trees adorned with golden and orange autumn leaves. Soft sunlight filters through the branches, casting gentle shadows on the ground, creating a peaceful setting for a nature walk.
Cabin in Blairstown
4.82 out of 5 average rating, 264 reviews

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.

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
5 out of 5 average rating, 210 reviews

Haven House Retreat In Tiny Home Village

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, 114 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

Popular amenities for Windsor vacation rentals

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