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, (34 reviews)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is CA $171
CA $266 total
includes taxes & fees
May 10 - May 11
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (61 reviews)
"We enjoyed our stay this was our second time look forward to doing again. "
United States
Gloria G.
The price is CA $109
CA $249 total
includes taxes & fees
May 13 - May 14
Cozy Home w/ Doggy Fence

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

Red cabin close to University of Central Missouri and Whiteman AF Base
Warrensburg
9.6 out of 10, Exceptional, (25 reviews)
"These places are amazing. Simple, but clean, and well Maintained. Great value for the money."
United States
Anthony
The price is CA $135
CA $173 total
includes taxes & fees
May 12 - May 13
Red 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, (2 reviews)
"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
The price is CA $135
CA $173 total
includes taxes & fees
May 27 - May 28
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

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.
The price is CA $164
CA $199 total
includes taxes & fees
May 11 - May 12
Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

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, (28 reviews)
"Perfect place to stay during a weekend family visit!"
United States
Terry M.
The price is CA $141
CA $233 total
includes taxes & fees
May 21 - May 22
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
Deepwater
10.0 out of 10, Exceptional, (46 reviews)
"Beautiful had everything we needed and was very peaceful "
United States
Raelynn W.
The price is CA $217
CA $371 total
includes taxes & fees
May 10 - May 11
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay!!!"
United States
Lynn W.
The price is CA $131
CA $245 total
includes taxes & fees
May 31 - Jun 1
Home Away From Home

Cabin 10 - Reel and Trigger

Cabin 10 - Reel and Trigger
Tom Township
10.0 out of 10, Exceptional, (1 review)
"We had family camping at the state park for the long weekend and wanted to stay close by. The cabin was perfect. We had time to visit easily and also an air conditioned place to sleep in. It also is dog friendly so we were able to bring the dogs. Getting a dog sitter on a long weekend is difficult. "
United States
Audrey B.
The price is CA $183
CA $216 total
includes taxes & fees
May 17 - May 18
Cabin 10 - Reel and Trigger

The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly
Knob Noster
10.0 out of 10, Exceptional, (16 reviews)
"Awesome clean place many amenities Would stay there again. "
United States
Marcia G.
The price is CA $139
CA $226 total
includes taxes & fees
May 31 - Jun 1
The Bungalow at WAFB/Knob Noster pet friendly

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, (15 reviews)
"The cabin was beautiful! Nice, quiet and cozy! Will definitely stay there again!"
United States
Cassie
The price is CA $190
CA $231 total
includes taxes & fees
May 17 - May 18
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Candlestick Suite

Candlestick Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Comfortable stay"
United States
David F.
The price is CA $158
CA $243 total
includes taxes & fees
May 10 - May 11
Candlestick Suite

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, (52 reviews)
"Very nice place to stay! Only stayed for a few hours because we were just passing through, but the beds were very comfortable!"
United States
Zachary B.
The price is CA $137
CA $222 total
includes taxes & fees
May 31 - Jun 1
Downtown Retreat with large privacy fenced yard. Pet Friendly!

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (17 reviews)
"Nice place to stay "
United States
Sam
The price is CA $114
CA $135 total
includes taxes & fees
Jun 2 - Jun 3
Hickory Hollow Resort

Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.4 out of 10, Exceptional, (48 reviews)
"Everything was great."
United States
Calvin S.
The price is CA $191
CA $317 total
includes taxes & fees
May 10 - May 11
Katy Trail Rest Stop

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.
The price is CA $165
CA $251 total
includes taxes & fees
May 31 - Jun 1
Peacock Suite

Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
The price is CA $135
CA $173 total
includes taxes & fees
May 25 - May 26
Cute Little Cabin #3

Unit B Country home apartment near Warrensburg

Unit B Country home apartment near Warrensburg
Warrensburg
8.8 out of 10, Excellent, (3 reviews)
"Amazing experience! Clean and comfortable. Easy drive to UCM. We would definitely stay here again!"
United States
Jason
The price is CA $135
CA $173 total
includes taxes & fees
May 17 - May 18
Unit B Country home apartment near Warrensburg

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, (7 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.
The price is CA $242
CA $874 total
includes taxes & fees
May 11 - May 12
Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade

Charming Micro Cabin 4 in the heart of the Ozarks

Charming Micro Cabin 4 in the heart of the Ozarks
Osceola
The price is CA $102
CA $135 total
includes taxes & fees
May 10 - May 11
Charming Micro Cabin 4 in the heart of the Ozarks
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.: This vacation home rental outside of Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.