Windsor Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Windsor

Smart TV, DVD player
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Holiday Home in 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 HK$973
HK$1,471 total
includes taxes & fees
9 Dec - 10 Dec
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Property grounds
Charming Micro Cabin 4 in the heart of the Ozarks

Holiday Home in Osceola

2.0 star property
The price is HK$467
HK$623 total
includes taxes & fees
9 Dec - 10 Dec
Charming Micro Cabin 4 in the heart of the Ozarks
Interior
Home Away From Home

Holiday Home in Warrensburg

10.0 out of 10, Exceptional, (30)
"Clean and cozy, the family and Iwould stay again"
United States
Patrick
The price is HK$740
HK$1,355 total
includes taxes & fees
9 Dec - 10 Dec
Home Away From Home
Outdoor dining
Cozy Home w/ Doggy Fence

Holiday Home in 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 HK$624
HK$1,403 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Home w/ Doggy Fence
Fridge, oven, stovetop, coffee/tea maker
Tan cabin close to University of Central Missouri and Whiteman AF Base

Cabin in Warrensburg

10.0 out of 10, Exceptional, (9)
"This is perfect for a quiet place to stay. The owner was very nice and helpful. I will stay here again if i am in the area."
United States
Carissa
The price is HK$849
HK$1,069 total
includes taxes & fees
9 Dec - 10 Dec
Tan cabin close to University of Central Missouri and Whiteman AF Base
Private kitchen
Unit A Country house near Warrensburg

Apartment in Warrensburg

2.0 star property
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 HK$849
HK$1,069 total
includes taxes & fees
9 Dec - 10 Dec
Unit A Country house near Warrensburg
Property grounds
Downtown Retreat with large privacy fenced yard. Pet Friendly!

Holiday Home in 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 HK$740
HK$1,199 total
includes taxes & fees
14 Dec - 15 Dec
Downtown Retreat with large privacy fenced yard. Pet Friendly!
Private kitchen
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

Holiday Home in Warrensburg

2.0 star property
The price is HK$716
HK$1,280 total
includes taxes & fees
6 Jan - 7 Jan 2026
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
Fridge, microwave, oven, stovetop
Cabin 12 - Reel and Trigger

Cabin in Tom Township

10.0 out of 10, Exceptional, (2)
"Great location quick easy access to boat ramps"
United States
Ron B.
The price is HK$1,458
HK$1,704 total
includes taxes & fees
14 Dec - 15 Dec
Cabin 12 - Reel and Trigger
Property grounds
Bunkhouse Cabin near Truman Lake in the Ozarks!

Cabin in Osceola

2.0 star property
The price is HK$623
HK$778 total
includes taxes & fees
9 Dec - 10 Dec
Bunkhouse Cabin near Truman Lake in the Ozarks!
Interior
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Cabin in Warrensburg

9.2 out of 10, Wonderful, (13)
"The cabin was beautiful! Nice, quiet and cozy! Will definitely stay there again!"
United States
Cassie
The price is HK$1,004
HK$1,236 total
includes taxes & fees
9 Dec - 10 Dec
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
Property grounds
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

Holiday Home in 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 HK$1,168
HK$2,385 total
includes taxes & fees
9 Dec - 10 Dec
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Property grounds
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard

Holiday Home in 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 HK$1,168
HK$2,385 total
includes taxes & fees
9 Dec - 10 Dec
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
Interior
Townhouse rentals of Sedalia

Apartment in Sedalia

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice and clean. Great area. Will definitely stay here again when we come back to sedalia"
United States
Kevin H.
The price is HK$1,518
HK$1,962 total
includes taxes & fees
12 Dec - 13 Dec
Townhouse rentals of Sedalia
Terrace/patio
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews

Holiday Home in Warsaw

10.0 out of 10, Exceptional, (77)
"I read all the reviews on this property and cannot understand how they are not all 10/10. Great location, great owners, great lake views and access, and great VIEW! Thank you again for sharing such a great place."
United States
Brian B.
The price is HK$1,114
HK$2,273 total
includes taxes & fees
9 Dec - 10 Dec
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
Smart TV
Scarlet Suite

Apartment in Sedalia Downtown Historic District

10.0 out of 10, Exceptional, (7)
"Great place "
United States
Francisco M.
The price is HK$1,103
HK$1,625 total
includes taxes & fees
22 Dec - 23 Dec
Scarlet Suite
Private kitchen
Cute Little Cabin #3

Cabin in warrensburg

2.0 star property
The price is HK$701
HK$856 total
includes taxes & fees
9 Dec - 10 Dec
Cute Little Cabin #3
Private kitchen
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

Cabin in Warrensburg

2.0 star property
The price is HK$701
HK$856 total
includes taxes & fees
9 Dec - 10 Dec
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Private kitchen
Hickory Hollow Resort

Cabin in Clinton

2.0 star property
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 HK$694
HK$816 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hickory Hollow Resort
Interior
The Bungalow at WAFB/Knob Noster pet friendly

Holiday Home in 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 HK$740
HK$1,204 total
includes taxes & fees
17 Dec - 18 Dec
The Bungalow at WAFB/Knob Noster pet friendly
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

Quality Inn

Quality Inn

10/10 Excellent
"Staff was great and hotel had the best amenities in the area."
Michael 2-night trip
Posted 4 days ago
Quality Inn

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

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO: This highly rated holiday home rental in Windsor is equipped with a BBQ, 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 that 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 wider area, you’ll find Whiteman Air Force Base and State Fair Community College.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip.