Windsor Holiday Rentals

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Our top choices for Windsor holiday 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)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is AU$286
includes taxes & fees
30 Dec - 31 Dec
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

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
9.4 out of 10, Exceptional, (22)
"Clean and comfortable stay"
United States
David F.
The price is AU$177
includes taxes & fees
30 Dec - 31 Dec
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.
2.0 star property
Warrensburg
10.0 out of 10, Exceptional, (1)
"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 AU$167
includes taxes & fees
30 Dec - 31 Dec
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)
"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 AU$271
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy Home w/ Doggy Fence

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (31)
"Great place to stay!!!"
United States
Lynn W.
The price is AU$262
includes taxes & fees
31 Dec - 1 Jan 2026
Home Away From Home

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
10.0 out of 10, Exceptional, (1)
"Easy communication, super convenient to our destination, clean."
United States
Roxanne B.
The price is AU$238
includes taxes & fees
8 Jan - 9 Jan 2026
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

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 AU$122
includes taxes & fees
30 Dec - 31 Dec
Cozy micro cabin 3 near Truman Lakes in the Ozarks

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 AU$239
includes taxes & fees
30 Dec - 31 Dec
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

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, (20)
"Great place to stay! "
United States
Keith H.
The price is AU$239
includes taxes & fees
30 Dec - 31 Dec
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

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 AU$233
includes taxes & fees
4 Jan - 5 Jan 2026
The Bungalow at WAFB/Knob Noster pet friendly

Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (20)
"Very easy check-in and very clean. It was a great location and we enjoyed our stay."
United States
Chad H.
The price is AU$235
includes taxes & fees
30 Dec - 31 Dec
Haven House New Comfortable and Clean Retreat

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, (44)
"We love staying here for the great location to UCM and the wonderful downtown area. "
United States
Michelle G.
The price is AU$232
includes taxes & fees
5 Jan - 6 Jan 2026
Downtown Retreat with large privacy fenced yard. Pet Friendly!

Bunkhouse Cabin near Truman Lake in the Ozarks!

Bunkhouse Cabin near Truman Lake in the Ozarks!
2.0 star property
Osceola
The price is AU$152
includes taxes & fees
30 Dec - 31 Dec
Bunkhouse Cabin near Truman Lake in the Ozarks!

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 AU$156
includes taxes & fees
27 Jan - 28 Jan 2026
Hickory Hollow Resort

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 AU$207
includes taxes & fees
30 Dec - 31 Dec
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, (22)
"Great place, location, and host! The house was very nice and exactly what we needed for the weekend!"
United States
Michael P.
The price is AU$250
includes taxes & fees
5 Jan - 6 Jan 2026
Fisher House Spacious Home in Tiny Home Village

Cute Little Cabin #3

Cute Little Cabin #3
2.0 star property
warrensburg
The price is AU$167
includes taxes & fees
30 Dec - 31 Dec
Cute Little Cabin #3

Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews

Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
Warsaw
10.0 out of 10, Exceptional, (77)
"My friends and I had an amazing stay! The hosts are extremely communicative, and the house is very clean and cozy. We really enjoyed our time out on the back porch looking at the lake, and we'll definitely be back again soon!"
United States
Sarah P.
The price is AU$439
includes taxes & fees
31 Dec - 1 Jan 2026
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews

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 AU$336
includes taxes & fees
31 Dec - 1 Jan 2026
Katy Trail Rest Stop

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 AU$461
includes taxes & fees
30 Dec - 31 Dec
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$177 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 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 Knob Noster State Park.

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.