Windsor Vacation Rentals

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Check prices for these dates

Tonight
Dec 17 - Dec 18
Tomorrow
Dec 18 - Dec 19
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

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

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Windsor
9.4 out of 10, Exceptional, (33)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is ￥19,346
￥29,401 total
includes taxes & fees
Dec 19 - Dec 20
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

Cozy Home w/ Doggy Fence
Warsaw
9.2 out of 10, Wonderful, (56)
"Loved the house and decor. Very close to the town of Warsaw and to our family and friends. Enjoy the stay!"
United States
Tina S.
The price is ￥12,397
￥27,889 total
includes taxes & fees
Dec 18 - Dec 19
Cozy Home w/ Doggy Fence
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

Green cabin close to University of Central Missouri and Whiteman AF Base
Warrensburg
9.4 out of 10, Exceptional, (15)
"Perfect size and spot for an easy stay "
United States
Charlie C.
The price is ￥15,322
￥19,581 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Green cabin close to University of Central Missouri and Whiteman AF Base
Fridge, microwave, oven, stovetop
Home Away From Home

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (31)
"Clean and cozy, the family and Iwould stay again"
United States
Patrick
The price is ￥14,703
￥26,930 total
includes taxes & fees
Dec 19 - Dec 20
Home Away From Home
Property grounds
Cozy micro cabin 3 near Truman Lakes in the Ozarks

Cozy micro cabin 3 near Truman Lakes in the Ozarks

Cozy micro cabin 3 near Truman Lakes in the Ozarks
2.0 star property
Osceola
The price is ￥9,286
￥12,381 total
includes taxes & fees
Dec 18 - Dec 19
Cozy micro cabin 3 near Truman Lakes in the Ozarks
Microwave, oven, stovetop
Bunkhouse Cabin near Truman Lake in the Ozarks!

Bunkhouse Cabin near Truman Lake in the Ozarks!

Bunkhouse Cabin near Truman Lake in the Ozarks!
2.0 star property
Osceola
The price is ￥12,382
￥15,477 total
includes taxes & fees
Dec 18 - Dec 19
Bunkhouse Cabin near Truman Lake in the Ozarks!
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

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Clinton
9.8 out of 10, Exceptional, (19)
"Needed a place to overnight during a fishing trip. Perfect for us. "
United States
moree30 m.
The price is ￥16,019
￥24,531 total
includes taxes & fees
Dec 18 - Dec 19
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Exterior
The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly
Knob Noster
10.0 out of 10, Exceptional, (14)
"Awesome clean place many amenities Would stay there again. "
United States
Marcia G.
The price is ￥14,703
￥23,927 total
includes taxes & fees
Dec 22 - Dec 23
The Bungalow at WAFB/Knob Noster pet friendly
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

Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
Warrensburg
9.2 out of 10, Wonderful, (14)
"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
The price is ￥19,965
￥24,577 total
includes taxes & fees
Dec 18 - Dec 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!

Downtown Retreat with large privacy fenced yard. Pet Friendly!
Warrensburg
10.0 out of 10, Exceptional, (43)
"Great property! Perfect for us for our visit to the Missouri State Fair. Quiet location, tastefully decorated. Excellent communications with owner. "
United States
ADRIAN F.
The price is ￥14,703
￥23,834 total
includes taxes & fees
Dec 21 - Dec 22
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Living area
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown 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
2.0 star property
Warrensburg
"Easy communication, super convenient to our destination, clean."
United States
Roxanne B.
The price is ￥12,382
￥23,340 total
includes taxes & fees
Dec 18 - Dec 19
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
Basic Cabin, Resort View | Terrace/patio
Hickory Hollow Resort

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.4 out of 10, Very Good, (13)
"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
The price is ￥13,790
￥16,224 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Hickory Hollow Resort
Living area
Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (19)
"Very easy check-in and very clean. It was a great location and we enjoyed our stay."
United States
Chad H.
The price is ￥19,362
￥24,146 total
includes taxes & fees
Dec 18 - Dec 19
Haven House New Comfortable and Clean Retreat
Smart TV
Peacock Suite

Peacock Suite

Peacock Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (3)
"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 ￥18,688
￥28,463 total
includes taxes & fees
Dec 26 - Dec 27
Peacock Suite
Private kitchen
Cute Little Cabin #3

Cute Little Cabin #3

Cute Little Cabin #3
2.0 star property
warrensburg
The price is ￥13,929
￥17,024 total
includes taxes & fees
Dec 18 - Dec 19
Cute Little Cabin #3
Private kitchen
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

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

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
2.0 star property
Warrensburg
"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 ￥13,929
￥17,024 total
includes taxes & fees
Dec 18 - Dec 19
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Smart TV, DVD player, books
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Warsaw
10.0 out of 10, Exceptional, (2)
"Very nice little place. Perfect place to stay for a fishing trip on Truman Lake. "
United States
Caleb T.
The price is ￥23,216
￥47,408 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Dining
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard

Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard

Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
Warsaw
10.0 out of 10, Exceptional, (1)
"Very peaceful area.. overnight stay.. convenient to everything.. highly recommend "
United States
David J.
The price is ￥23,216
￥47,408 total
includes taxes & fees
Dec 18 - Dec 19
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
Dining
Unit A Country house near Warrensburg

Unit A Country house near Warrensburg

Unit A Country house near Warrensburg
2.0 star property
Warrensburg
10.0 out of 10, Exceptional, (2)
"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.
The price is ￥16,870
￥21,247 total
includes taxes & fees
Dec 18 - Dec 19
Unit A Country house near Warrensburg
Dining
Katy Trail Rest Stop

Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.4 out of 10, Exceptional, (46)
"Lovely property and just the right distance to everything. "
United States
JODI B.
The price is ￥20,120
￥34,181 total
includes taxes & fees
Dec 21 - Dec 22
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

Hampton Inn Sedalia

Hampton Inn Sedalia

10/10 Excellent
"Excellent place to stay everything was to satisfaction room was very clean. "
Alexandr 2-night trip
Posted 6 days ago
Hampton Inn Sedalia

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?

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 State Fair Community College.

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.