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

4.96 out of 5 average rating, 122 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, 165 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.

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, 169 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

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

5 out of 5 average rating, 108 reviews

Beautiful Grain Bin Cabin, 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 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, 289 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, 170 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.

Superhost

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

4.81 out of 5 average rating, 254 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, 185 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

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, 32 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.

Top guest favorite

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, 101 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.

Guest favorite

A single-story home with a light gray exterior and white trim is set among greenery. A vibrant red bush adds color to the front yard, and a path leads to the entrance. Large windows allow natural light to illuminate the interior.

Home in Knob Noster

4.9 out of 5 average rating, 108 reviews

•Cozy 2 BR Home Away from Home•

Welcome home! Centrally located in downtown Knob Noster, your family will have everything it needs to enjoy a comfortable stay. We welcome long term guests, and your pets! If your dates are unavailable please inquire as to additional options we may have. We have special rates for longer stays and military families

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, 188 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.