Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favourite
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, 108 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.

Guest favourite
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 favourite
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, 359 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!

Top guest favourite
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
4.99 out of 5 average rating, 159 reviews

The Highland GrainBin, 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 favourite
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, 277 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 favourite
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, 310 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 favourite
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 favourite
A row of historic buildings with varied brick facades lines a tree-lined street. Large windows and signage are visible on the storefronts. In the background, a water tower stands prominently, emphasizing the urban setting. The street appears well-maintained and accessible.
Loft in Sedalia
4.97 out of 5 average rating, 119 reviews

“The Loft” in the Heart of Downtown Sedalia

Built in 1880, the building is on the national Historic Register. The Loft is a fully updated, 1500 sq ft, 2 bed, 2 bath space with off-street parking, a shed to secure your bikes for the trail, 12x20 deck with grill and table seating. Keyless entry at deck entry and front entrance, wi-fi, smart tv’s and so so much more. Coffee Bar, all new furniture and appliances. Easy walk to all downtown Sedalia has to offer including a gym, which is just a few blocks away.

Top guest favourite
Cabin in Camdenton
4.94 out of 5 average rating, 307 reviews

Chatham Cabin-Home of the Midwest Sunset!

Cozy cabin offers incredible lake views and lake access including boat dock with swim platform and swim ladder and fish sink and boat slips. Cabin includes a kitchenette with stove and all the kitchen essentials for cooking and staying in. Bath includes a 6 foot claw-foot tub w/shower. Nestled on a quiet lake road “Isle View” will not disappoint. We are close to Ha Ha Tonka State Park, Kinderhook golf course or Lake Valley golf course and Ball Park Nationals.

Guest favourite
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 favourite
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, 211 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

Top guest favourite
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, 117 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