Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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Top Guest favourite
The spacious camper is illuminated in the evening light, showcasing its modern design. Steps lead up to the entrance, and outdoor seating is arranged nearby. A fire pit sits in the foreground, surrounded by landscaped gravel and soft lighting that enhances the tranquil setting.
Campervan/RV in Warsaw
4.96 out of 5 average rating, 206 reviews

Private Waterfront Relaxation at Peppermint Cove!

Our spacious camper is lake front with a gorgeous Cove view, sitting on our quiet, peaceful, private property on a private road. No sharing our space, and a 200 ft walk (across from camper) to the water, enjoy our dock with amenities, shady green space by the water, or the outdoor kitchen, patio and firepit at the camper. You’ll have access to our HOA boat ramp. We’re located on the Osage River Arm of Lake of the Ozarks on MM 84 (@ the power lines) and 15 minutes away from Truman Dam and Lake.

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, 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!

Superhost
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
4.81 out of 5 average rating, 137 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!

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, 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 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.

Guest favourite
The exterior of the log home is displayed, featuring a peaked roof and large windows that allow for natural light. Surrounding greenery includes trimmed bushes and an open lawn area, creating a welcoming appearance. The structure stands prominently against a clear blue sky.
Home in Concordia
4.87 out of 5 average rating, 166 reviews

Charming Log Home

Come enjoy our log home! This home was built as a model log home. It has its own charm and beauty and is a great place to unwind if you don’t mind some road noise. High speed internet is available-but no TV The property is convenient and easy to access,with a large parking area, although being next to I70 it is not quiet and secluded, expect road noise.( ear plugs and white noise machines are provided.) There is no Laundry-A local Laundromat is available.

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, 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

Top Guest favourite
An open concept dining and living area is visible, featuring a large table surrounded by black chairs. The well-appointed kitchen is equipped with wooden cabinetry and ample counter space. A cozy seating area includes a light-colored sofa and a small table, with natural light illuminating the space.
Home in Hughesville
4.99 out of 5 average rating, 119 reviews

Walnut Grove Retreat

Quiet country house on a wooded lot. Entire main floor of this secluded country home, with a covered deck overlooking woods, including outdoor dining and lounge. Well appointed kitchen with open concept dining and living area. Eight miles to Sedalia, the Katy Trail and Missouri State Fairgrounds. Thirty minutes to Whiteman AFB. We welcome up to two dogs.

Top Guest favourite
A tranquil view of the cabin from a rocky creek bank, surrounded by lush greenery and trees. The sunset casts a warm glow on the cabin, enhancing its rustic charm. Gentle ripples are seen in the creek, reflecting the evening colors of the sky.
Cabin in Adair Township
4.98 out of 5 average rating, 258 reviews

Cabin on the Creek, 120 Acres

Located at the confluence of two creeks, in real Missouri Ozarks, sits our Cabin. Quant and cozy, this old “hunting cabin” and surrounding land have much to offer. Within the 120 acres of private property, yours to explore, are numerous flowing creeks, ponds, springs, fields, and rolling wooded hills. All ready for your getaway.

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, 192 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.

Guest favourite
A charming cottage is nestled within a serene countryside setting, illuminated by soft outdoor lighting. Large windows reflect warm interior light, while a lush lawn and mature trees provide a peaceful backdrop. The walkway is lined with subtle lighting, enhancing the inviting ambiance.
Home in Calhoun
4.72 out of 5 average rating, 99 reviews

Tropical Country Cottage

Relax with the whole family at this peaceful place to stay. Access to 3 acres of countryside property with plenty of room to enjoy. Less than a mile from the Katy Trail; perfect for riding bikes and exploring. Also near Truman Lake; great for fishing and relaxing by the water!

Popular amenities for Windsor holiday rentals

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