Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Windsor vacation rentals

Exterior

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 ￥19,798
￥30,866 total
includes taxes & fees
May 20 - May 21
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Children's area

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
8.8 out of 10, Excellent, (65 reviews)
"We enjoyed our stay this was our second time look forward to doing again. "
United States
Gloria G.
The price is ￥12,686
￥28,697 total
includes taxes & fees
May 19 - May 20
Cozy Home w/ Doggy Fence
Private kitchen

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 ￥15,680
￥20,020 total
includes taxes & fees
May 29 - May 30
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Seasonal outdoor pool

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.0 out of 10, Very Good, (18 reviews)
"Nice place to stay "
United States
Sam
The price is ￥11,150
￥13,451 total
includes taxes & fees
Jun 15 - Jun 16
Hickory Hollow Resort
Interior

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 ￥15,680
￥20,020 total
includes taxes & fees
May 17 - May 18
Red cabin close to University of Central Missouri and Whiteman AF Base
Private kitchen

Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
The price is ￥15,715
￥20,064 total
includes taxes & fees
May 21 - May 22
Cute Little Cabin #3
Interior

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 ￥16,392
￥27,005 total
includes taxes & fees
May 18 - May 19
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Interior

Unit B Country home apartment near Warrensburg

Unit B Country home apartment near Warrensburg
Warrensburg
8.6 out of 10, Excellent, (4 reviews)
"Wifi issues, but luckily we were too busy to care. Property was nice and owners were very helpful"
United States
Mary K H.
The price is ￥15,680
￥20,020 total
includes taxes & fees
May 17 - May 18
Unit B Country home apartment near Warrensburg
Fridge, microwave, oven, stovetop

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 ￥15,204
￥28,454 total
includes taxes & fees
May 27 - May 28
Home Away From Home
Interior

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
9.4 out of 10, Exceptional, (16 reviews)
"The cabin was beautiful! Nice, quiet and cozy! Will definitely stay there again!"
United States
Cassie
The price is ￥22,015
￥26,828 total
includes taxes & fees
May 18 - May 19
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
Smart TV, fireplace, books

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, (53 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 ￥15,680
￥25,509 total
includes taxes & fees
Jun 1 - Jun 2
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Exterior

The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly
Knob Noster
10.0 out of 10, Exceptional, (17 reviews)
"Awesome clean place many amenities Would stay there again. "
United States
Marcia G.
The price is ￥15,521
￥25,463 total
includes taxes & fees
May 19 - May 20
The Bungalow at WAFB/Knob Noster pet friendly
TV

Sleeps 5|King Beds|Comfortable Stay|Warrensburg

Sleeps 5|King Beds|Comfortable Stay|Warrensburg
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.
The price is ￥19,006
￥67,534 total
includes taxes & fees
May 18 - May 19
Sleeps 5|King Beds|Comfortable Stay|Warrensburg
Living area

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)
"Immaculate and lovely, check-in was super easy and location perfect."
United States
Sabrina D.
The price is ￥17,263
￥21,721 total
includes taxes & fees
May 31 - Jun 1
Green cabin close to University of Central Missouri and Whiteman AF Base
1 bedroom, WiFi, bed sheets

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 ￥18,293
￥28,223 total
includes taxes & fees
May 21 - May 22
Candlestick Suite
Smart TV

Rolly's house home away from home

Rolly's house home away from home
Warsaw
8.0 out of 10, Very Good, (2 reviews)
"It was a nice little old house . I thought it was better then a hotel for sure no body banging doors or any other ppl to worry about so that was nice "
United States
Kevin C.
The price is ￥17,105
￥25,285 total
includes taxes & fees
May 18 - May 19
Rolly's house home away from home
Smart TV, fireplace, books, music library

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, (6 reviews)
"Easy communication, super convenient to our destination, clean."
United States
Roxanne B.
The price is ￥18,372
￥30,502 total
includes taxes & fees
Jun 1 - Jun 2
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
Fridge, microwave, coffee/tea maker, toaster

Cabin 2 - Reel and Trigger

Cabin 2 - Reel and Trigger
Tom Township
The price is ￥21,183
￥24,986 total
includes taxes & fees
May 28 - May 29
Cabin 2 - Reel and Trigger
Smart TV

The Conservatory

The Conservatory
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (11 reviews)
"We absolutely loved our stay!! The entire building and our place had so much character while still being modern and updated. "
United States
Brooke M.
The price is ￥34,923
￥49,136 total
includes taxes & fees
May 17 - May 18
The Conservatory
Smart TV

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 ￥19,124
￥29,286 total
includes taxes & fees
May 31 - Jun 1
Peacock Suite
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Residential Suites Warrensburg by Hotel O US 50

Residential Suites Warrensburg by Hotel O US 50

2/10 Terrible
"Room spelled like smoke, and musty, dirty fork in the chair. Would not recommend at all"
Tiffany 1-night trip
Posted 1 day ago
Residential Suites Warrensburg by Hotel O US 50

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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 Harry S. Truman 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.