Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A modern bathroom is visible, featuring a sleek vanity with dual sinks. A dark shower curtain, emblazoned with 'Whistle House,' provides privacy. Neatly arranged towels are stored on open shelves, while warm lighting enhances the inviting atmosphere. Light-colored tiles complement the wooden flooring.

Apartment in Sedalia

4.98 out of 5 average rating, 230 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.

Guest favorite

The entrance features a white front door framed by two windows. A welcome mat is placed on the concrete step, and a small decorative flower pot with blooming plants is positioned to the side, enhancing the welcoming appearance of the entryway.

Home in Clinton

4.95 out of 5 average rating, 107 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 deck area features several seating options, including two reclining chairs and a round accent chair. The wooden deck is surrounded by trees, providing a shaded outdoor space for relaxation.

Home in Deepwater

4.95 out of 5 average rating, 108 reviews

A Cozy Getaway

Minutes away from Harry S. Truman Dam & Reservoir & the upper end of the Lake of the Ozarks. The lake is a popular fishing destination for crappie, largemouth bass, hybrid stripers, catfish, as well as some of the Nation's finest snagging for spoonbill paddlefish. The surrounding area (110,000 acres) provides plentiful & diverse opportunities, including hiking, horseback riding, golfing, biking, bonfires, bird watching, off-road vehicle adventures, & some of the best hunting in the country.

Top guest favorite

A wooden deck, crafted from planks, extends into a privacy-fenced backyard. A barbecue grill is positioned on the deck for outdoor cooking. The yard is mostly cleared, with a few patches of grass visible, and surrounding trees provide a natural setting.

Home in Warrensburg

4.99 out of 5 average rating, 149 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 comfortable living area features a grey sectional sofa with light cushions, a black coffee table, and a planter with a leafy green plant. A television is mounted on a stand opposite the seating, while natural light enters through a large window covered with horizontal blinds.

Apartment in Sedalia

4.84 out of 5 average rating, 159 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

A spacious bathroom is featured, with laundry appliances integrated into the design. A large vanity with storage sits opposite the shower area, which is enclosed with a curtain. Blue accent rugs and a laundry-themed mat add color to the neutral tile floor.

Home in Sedalia

4.91 out of 5 average rating, 120 reviews

Country house surrounded by woods, close to town.

Great way to get away with your family or alone. Nice country setting on asphalt road. Master bedroom includes an outside entry to a private deck and a queen bed. The 2nd bedroom comes with 2 twin beds. The 3rd bedroom has a full sized bed. The bathroom is very large with an entry from the master and the hall and includes the washer and dryer. Patio for grilling or just enjoying the scenery. Only 20 min from Truman Lake.10 minutes from Missouri State Fairgrounds.

Top guest favorite

Guest suite in Sedalia

4.98 out of 5 average rating, 166 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 brick exterior home is seen with a well-manicured lawn and landscaping. Soft lighting illuminates the entrance, where a welcoming front door is framed by decorative details. A clear path leads from the sidewalk to the door, enhancing accessibility.

Home in Sedalia

5 out of 5 average rating, 172 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 modern living space showcases a light gray sectional sofa positioned near an espresso-colored coffee table. The kitchen features sleek white cabinetry and stainless-steel appliances. A dining area is visible, equipped with a dark table and high-backed chairs, illuminated by overhead lighting.

Home in Windsor

4.86 out of 5 average rating, 28 reviews

Windsor Blueberry

Freshly renovated 2BR in central Windsor—perfect for Katy Trail trips or nearby weddings (The Moment & Evelyn Valley Ranch)! Sleeps 4 with comfy beds, WiFi, Smart TV, full kitchen, coffee station, and laundry. Relax on the deck with bike ramp + indoor storage. Quiet neighborhood close to trailheads. Pet-friendly (2 dogs under 25lbs, $25/night). Bathroom essentials included for a cozy, carefree stay!

Superhost

A dirt path is framed by lush greenery, leading into a shaded forest. Signs indicate the beginning of a trail, and a wooden gate is visible on either side. The serene atmosphere is highlighted by the soft light filtering through the trees overhead.

Home in Windsor

4.88 out of 5 average rating, 181 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Windsor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Windsor

Guest favorite

A wooden deck is accessed by a set of stairs, providing a simple outdoor seating option. A single chair is positioned near the railing, with trees visible in the background. The clear blue sky adds to the serene atmosphere of the cabin setting.

Cabin in Warsaw

4.88 out of 5 average rating, 17 reviews

The Cabin in the Woods/Ranch Setting/Warsaw, MO

WillRating, 5 stars1 week ago

Awesome cabin in the woods. very peaceful and quiet. Lots to do around the area. Will definitely be back

Guest favorite

A serene pond is surrounded by lush greenery, reflecting blue skies and puffy clouds above. A wooden deck with two lounge chairs and a small table offers a tranquil seating area. A fountain in the pond enhances the peaceful ambiance.

Farm stay in Clinton

5 out of 5 average rating, 9 reviews

Peaceful Farmstay@ Boulder Hollow nearTrumanLake

MatteaRating, 5 stars8 months ago

Absolutely loved this stay. Stopped here on the way back from a very stressful business trip, & was met with coziness, everything thought of & already provided, the comfiest mattress I’ve slept on at any airbnb…all kinds of good stuff! Sat out on a rock by the pond & fed excited catfish. Drank coffee on their absolutely perfect porch. Felt peace for the first time in over a week. Very needed. Plan to stop here again. Hosts were also very accommodating with such a last minute stay, & were extremely pleasant, providing help & guidelines while still giving space. It was simply lovely, & I can’t recommend this place enough.

Top guest favorite

The exterior entrance of the house is highlighted by soft lighting and features a stone facade with wooden accents. Flanking the path, lush greenery and ornamental grasses create a welcoming atmosphere. The sky transitions to dusk, adding a serene backdrop.

Cabin in Sedalia

4.98 out of 5 average rating, 44 reviews

Elegant Modern Retreat | Custom Décor Luxe Comfort

GailRating, 5 stars2 weeks ago

it was a wonderful day and the pictures were accurate. Accomadations were wonderul and small extras made big impact.

Top guest favorite

A front porch swing is positioned on a wooden deck, adorned with navy and cream decorative pillows. A welcome mat with a friendly greeting is placed at the black entrance door, surrounded by greenery and seasonal decor on the wall.

Bungalow in Warrensburg

4.98 out of 5 average rating, 53 reviews

Cheerful Blue-Roof Bungalow

MattRating, 5 stars2 weeks ago

we feel right at home. We have stayed here before and we have plans to stay here in the future. It’s a cute home and very comfortable.

Guest favorite

A wooden shelf is mounted on a textured wall with natural wood and metal accents. A jar filled with fresh flowers adds a touch of color, while a small decor sign reading 'Lake Life' sits nearby, enhancing the room's outdoor theme.

Cabin in Warsaw

4.89 out of 5 average rating, 72 reviews

Lil' Minnow Cottage Cabin

LaTroyaRating, 5 stars1 month ago

LOVED LOVED LOVED THE CABIN!!! .. David and his Wife Heidi were amazing!!!! .. I felt very welcomed and safe while staying there .. My kids really enjoyed the space especially the loft bed! .. They only place i wanna stay while I visit!!! THANK YALL SO MUCH! 💜 .. 10/10

Guest favorite

A quaint street scene features the Warsaw Antique Mall with a prominent sign, flanked by charming storefronts and a parked truck. Lush trees line the street, while a green bench and trash receptacle add to the inviting atmosphere of the local community.

Home in Warsaw

4.94 out of 5 average rating, 321 reviews

The Overlook

JenniferRating, 5 stars3 days ago

If you haven’t ever been to the Overlook, you need to! Absolutely our favorite spot! Ryan is a fantastic host that always goes the extra mile!

A living area features a large television mounted on a wall opposite two comfortable recliners. Natural light fills the space through sliding glass doors that lead to a deck. A rustic cabinet and decorative clock add character to the space.

Home in Lincoln

5 out of 5 average rating, 5 reviews

The Hideaway

SarahRating, 5 stars2 weeks ago

The cabin was clean and welcoming. I immediately loved it and felt right at home. We enjoyed the porch. The front porch has a nice porch swing and table to enjoy a meal or morning coffee. The back has a cute fire pit and chairs. Nice smart tv with all the channels and streaming services. Furniture was comfortable. Kitchen fully stocked and they left us a couple snacks which was a very nice touch. Even some bottled water in the fridge which was nice. Supplied soaps and shampoo in the shower with nice shower head. My only recommendation would be to upgrade the pillows to higher quality and maybe the sheets also. Overall not much else to improve on. We drove into Buffalo creek area and explored some areas of the creek. There are some really good places to eat for such a small area. Estes drive in had an exceptional hamburger and ice cream. Maces inn had a good meal. Mozarka coffee shop is excellent and also had food items. We explored nearby Cole Camp also. Perfect for a weekend away.

Guest favorite

An open living area features exposed brick walls and wooden beams, combined with modern furnishings. A spacious couch is placed in front of a light-colored armchair. A dining table for four is positioned next to the kitchen, which is equipped with stainless steel appliances.

Apartment in Sedalia

5 out of 5 average rating, 41 reviews

The Senator’s Loft Downtown Sedalia

JustinRating, 5 stars1 week ago

The Senator's Loft is a fantastic place to stay if you ever need to come to downtown Sedalia!

Show all

Vacation rentals in Windsor

Top-rated vacation rentals in Windsor

Vacation rentals for every style

Popular amenities for Windsor vacation rentals

Other great vacation rentals in Windsor

Destinations to explore