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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor holiday rentals

A small, single-story house with a porch, a front door, and a small window on the side.

1. 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, (37 reviews)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is AU$275
includes taxes & fees
31 Aug - 1 Sept
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

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

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Warrensburg
9.6 out of 10, Exceptional, (5 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 AU$179
includes taxes & fees
31 Aug - 1 Sept
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
A row of cabins with wooden decks and stairs leading to the entrance.

3. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (23 reviews)
"Nice place to stay "
United States
Sam
The price is AU$146
includes taxes & fees
31 Aug - 1 Sept
Hickory Hollow Resort
A cozy cabin interior with a kitchen, dining area, and a sofa.

4. 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, (29 reviews)
"Clean and spacious, ac worked very well :)"
United States
Kelly G.
The price is AU$179
includes taxes & fees
31 Aug - 1 Sept
Red cabin close to University of Central Missouri and Whiteman AF Base

5. Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
The price is AU$179
includes taxes & fees
31 Aug - 1 Sept
Cute Little Cabin #3
A spacious loft-style room with a wooden interior, a staircase, a sofa, and a television.

6. 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, (19 reviews)
"Excellent stay"
United States
Michael E.
The price is AU$239
includes taxes & fees
31 Aug - 1 Sept
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
A compact kitchen with a stove, sink, and refrigerator, a wooden dining area with stools, and a gray sofa in a cabin-style interior.

7. 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 AU$179
includes taxes & fees
31 Aug - 1 Sept
Unit B Country home apartment near Warrensburg
A single-story house with a covered porch, a front door, and a mailbox.

8. The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly
Knob Noster
10.0 out of 10, Exceptional, (18 reviews)
"Had a great stay. It was clean and we had everything we needed!"
United States
Lindsay E.
The price is AU$232
includes taxes & fees
8 Sept - 9 Sept
The Bungalow at WAFB/Knob Noster pet friendly
A cozy cabin interior with a wooden staircase, a sofa, a chair, and a refrigerator.

9. 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
9.2 out of 10, Wonderful, (20 reviews)
"Immaculate and lovely, check-in was super easy and location perfect."
United States
Sabrina D.
The price is AU$194
includes taxes & fees
31 Aug - 1 Sept
Green cabin close to University of Central Missouri and Whiteman AF Base
A kitchen with a wooden floor, white cabinets, a black refrigerator, and a wooden bench.

10. Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (47 reviews)
"Place was excellent!!"
United States
Garrett
The price is AU$254
includes taxes & fees
8 Sept - 9 Sept
Home Away From Home
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island.

11. Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (38 reviews)
"Awesome place to stay in Sedalia, beautiful cosy home. Top notch host. Would definitely recommend and stay again."
Canada
James
The price is AU$272
includes taxes & fees
14 Sept - 15 Sept
Haven House New Comfortable and Clean Retreat
A living room with a fireplace, a television mounted above it, and a sofa.

12. 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, (64 reviews)
"Nice place to stay in Warrensburg"
United States
Jon S.
The price is AU$223
includes taxes & fees
9 Sept - 10 Sept
Downtown Retreat with large privacy fenced yard. Pet Friendly!
A park with a playground, a bench, a lamppost, and a view of a lake.

13. Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (70 reviews)
"Host was easy to contact/ house was clean."
United States
Prentiss E.
The price is AU$253
includes taxes & fees
2 Sept - 3 Sept
Cozy Home w/ Doggy Fence
A compact kitchen with wooden cabinets, a white refrigerator, a stove, and a sink.

14. Cabin 3 - Reel and Trigger

Cabin 3 - Reel and Trigger
Tom Township
9.4 out of 10, Exceptional, (3 reviews)
"We enjoy our stay. The location is awesome. No hassles."
United States
April G.
The price is AU$223
includes taxes & fees
1 Sept - 2 Sept
Cabin 3 - Reel and Trigger
A cozy living room with a wooden ceiling, a ceiling fan, a large flat-screen TV, a sofa, and a coffee table.

15. 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, (50 reviews)
"Perfect getaway to relax. We enjoyed our trip and will be booking again!"
United States
Cynthia M.
The price is AU$324
includes taxes & fees
2 Sept - 3 Sept
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
A cozy cabin interior with a wooden staircase, a sofa, a chair, and a refrigerator.

16. Tan cabin close to University of Central Missouri and Whiteman AF Base

Tan cabin close to University of Central Missouri and Whiteman AF Base
Warrensburg
10.0 out of 10, Exceptional, (15 reviews)
"Great location for our needs "
United States
Stephen B.
The price is AU$209
includes taxes & fees
31 Aug - 1 Sept
Tan cabin close to University of Central Missouri and Whiteman AF Base

17. Truman Lake Getaway!! 1 bedroom comfy RV

Truman Lake Getaway!! 1 bedroom comfy RV
Warsaw
8.0 out of 10, Very good, (4 reviews)
"Julie and Sam were friendly and helpful. Place was clean, cozy, and close to everything we needed... ample room to park a boat and truck/car. Pet friendly is always a plus. Will return again!!!!!"
United States
Shirley V.
The price is AU$186
includes taxes & fees
31 Aug - 1 Sept
Truman Lake Getaway!! 1 bedroom comfy RV
A two-story house with a stone facade, a number '2713' above the door, and a well-maintained lawn.

18. Fisher House Spacious Home in Tiny Home Village

Fisher House Spacious Home in Tiny Home Village
Sedalia
10.0 out of 10, Exceptional, (35 reviews)
"Can’t wait to stay again"
United States
Caleb B.
The price is AU$272
includes taxes & fees
7 Sept - 8 Sept
Fisher House Spacious Home in Tiny Home Village
A spacious dining area with a high ceiling fan, a kitchen with wooden cabinets, and a large window providing natural light.

19. Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.2 out of 10, Wonderful, (52 reviews)
"We had a great stay at The Katy Rest Stop. The host provided all information (check-in process, check-in and check-out info, and procedures) in a friendly and timely manner. The host responded to questions promptly, too. The property was clean and well maintained. Since we have family in Sedalia, we’ll certainly consider using it again should the need arise."
United States
Kim
The price is AU$339
includes taxes & fees
13 Sept - 14 Sept
Katy Trail Rest Stop
A living room with a fireplace, a television mounted above it, and a patterned rug on the floor.

20. 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, (11 reviews)
"The rooms were lovely, clean, and comfortable. The bed was of the best we've had in a VRBO so far."
United States
Wendy P.
The price is AU$295
includes taxes & fees
1 Sept - 2 Sept
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
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

Holiday Inn Express & Suites Warrensburg North by IHG

Holiday Inn Express & Suites Warrensburg North by IHG

10/10 Excellent
"Very nice and clean."
Michael 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Warrensburg North by IHG

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$146 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?

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.: This holiday home rental outside of Windsor is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.