Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Windsor
9.4 out of 10, Exceptional, (33 reviews)
"Perfect stop right on the Katy Trail! All was just as described in the listing. Close to shopping areas to stock up on food and supplies. Sent stay request on Friday after 6pm to arrive on Saturday and host replied within an hour that late reservation was no problem and property would be ready for my stay. "
United States
Pat K.
$180 nightly
The price is $189
Feb 10 - Feb 11
Total with taxes and fees
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Green cabin close to University of Central Missouri and Whiteman AF Base

Green cabin close to University of Central Missouri and Whiteman AF Base
Warrensburg
9.6 out of 10, Exceptional, (17 reviews)
"Everything was as advertised."
United States
William B.
$119 nightly
The price is $127
Feb 10 - Feb 11
Total with taxes and fees
Green cabin close to University of Central Missouri and Whiteman AF Base

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Warrensburg
10.0 out of 10, Exceptional, (1 review)
"The cabins are brand new, very clean very nice very spacious. I absolutely love to stay and will definitely be back in refer to family and friends."
United States
Melanie
$110 nightly
The price is $110
Feb 10 - Feb 11
Total with taxes and fees
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.2 out of 10, Wonderful, (56 reviews)
"Very gracious host!"
United States
rachell c.
$170 nightly
The price is $180
Feb 10 - Feb 11
Total with taxes and fees
Cozy Home w/ Doggy Fence

Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
Warrensburg
9.2 out of 10, Wonderful, (14 reviews)
"The cabin had all that our family needed for the weekend. The size of the cabin is very unassuming but quite large and spacious. Enough for everyone to have their own space. Excellent "
United States
Tasha
$149 nightly
The price is $159
Feb 10 - Feb 11
Total with taxes and fees
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Downtown Retreat with large privacy fenced yard. Pet Friendly!

Downtown Retreat with large privacy fenced yard. Pet Friendly!
Warrensburg
10.0 out of 10, Exceptional, (46 reviews)
"We love staying here for the great location to UCM and the wonderful downtown area. "
United States
Michelle G.
$145 nightly
The price is $154
Feb 10 - Feb 11
Total with taxes and fees
Downtown Retreat with large privacy fenced yard. Pet Friendly!

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.6 out of 10, Excellent, (14 reviews)
"Our cabin was clean, comfortable and affordable. The check-in was effortless and we had no issues with the stay. I would recommend the place to friends and family traveling through the area."
United States
Terry
$99 nightly
The price is $105
Mar 10 - Mar 11
Total with taxes and fees
Hickory Hollow Resort

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay!!!"
United States
Lynn W.
$165 nightly
The price is $174
Feb 17 - Feb 18
Total with taxes and fees
Home Away From Home

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points
Osceola
10.0 out of 10, Exceptional, (1 review)
"Very quiet and peaceful. The interior was clean and updated. Nice living room with 3 love seats, which I think are also pull-out beds? And there is a card table with sturdy comfortable chairs that can seat maybe 6 people. There is a small, but very nice kitchen. Two bathrooms, each attached to its own bathroom, with the bathrooms also having a second door opening to the living room for convenience. Beds were comfortable, but just note for guests who are bigger or have mobility issues, the beds...
United States
Douglas H.
$140 nightly
The price is $140
Feb 10 - Feb 11
Total with taxes and fees
Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

Candlestick Suite

Candlestick Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Comfortable stay"
United States
David F.
$166 nightly
The price is $178
Feb 10 - Feb 11
Total with taxes and fees
Candlestick Suite

Cozy 2BR_Near UCM_King_Beds|Family Friendly

Cozy 2BR_Near UCM_King_Beds|Family Friendly
Warrensburg
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay here and would definitely recommend for couples or small families."
United States
Richard W.
$407 nightly
The price is $407
Feb 10 - Feb 11
Total with taxes and fees
Cozy 2BR_Near UCM_King_Beds|Family Friendly

Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (24 reviews)
"Very easy check-in and very clean. It was a great location and we enjoyed our stay."
United States
Chad H.
$145 nightly
The price is $156
Feb 10 - Feb 11
Total with taxes and fees
Haven House New Comfortable and Clean Retreat

Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
Warrensburg
10.0 out of 10, Exceptional, (2 reviews)
"Easy communication, super convenient to our destination, clean."
United States
Roxanne B.
$169 nightly
The price is $184
Feb 10 - Feb 11
Total with taxes and fees
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

Cozy studio shotgun apartment in the heart of the Ozarks

Cozy studio shotgun apartment in the heart of the Ozarks
Osceola
$84 nightly
The price is $84
Feb 10 - Feb 11
Total with taxes and fees
Cozy studio shotgun apartment in the heart of the Ozarks

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Clinton
9.8 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Keith H.
$170 nightly
The price is $170
Feb 23 - Feb 24
Total with taxes and fees
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

Peacock Suite

Peacock Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was exactly as described and perfectly located for my trip. I had a wonderful stay and would definitely book again!" "
United States
Mark S.
$171 nightly
The price is $184
Feb 10 - Feb 11
Total with taxes and fees
Peacock Suite

Unit A Country house near Warrensburg

Unit A Country house near Warrensburg
Warrensburg
10.0 out of 10, Exceptional, (3 reviews)
"Great little spot with a neat community. Store right next door and everything else you would want within 10 minutes or so. "
United States
Cameron C.
$129 nightly
The price is $137
Feb 10 - Feb 11
Total with taxes and fees
Unit A Country house near Warrensburg

Fisher House Spacious Home in Tiny Home Village

Fisher House Spacious Home in Tiny Home Village
Sedalia
10.0 out of 10, Exceptional, (23 reviews)
"Outstanding place to stay. Very clean!!"
United States
Aaron D.
$154 nightly
The price is $166
Feb 10 - Feb 11
Total with taxes and fees
Fisher House Spacious Home in Tiny Home Village

Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade

Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade
Warsaw
10.0 out of 10, Exceptional, (6 reviews)
"We wanted a place close to the lake and this was perfect. Super clean and just a beautiful layout all around. The neighborhood felt safe and friendly. I wouldn't look any further if im planning another trip to the area as i will check with this place first "
United States
Christopher E.
$600 nightly
The price is $600
Feb 10 - Feb 11
Total with taxes and fees
Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade

Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.4 out of 10, Exceptional, (47 reviews)
"Work crew stayed here during an out of town project. They were very happy with the accomodations and commented how much nicer and spacious this stay was over a hotel room.The host was great to work with, I would definately book again for a work trip, or even for a family getaway to Sedalia."
United States
Shadyia W.
$200 nightly
The price is $218
Feb 10 - Feb 11
Total with taxes and fees
Katy Trail Rest Stop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $117 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we offer vacation rentals near top points of interest in Windsor, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Windsor?

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO: This Windsor vacation home rental is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Leisure Park, or get out into nature at a spot like Harry S Truman Reservoir. In the larger area, you’ll find Whiteman Air Force Base and Knob Noster State Park.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Windsor. Vacation rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family getaway.