Default HTG hotel image

Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

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, (36 reviews)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is NZ$329
includes taxes & fees
19 Aug - 20 Aug
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

2. Walk to State Fairgrounds & Katy Trail, 4BR Home by Park

Walk to State Fairgrounds & Katy Trail, 4BR Home by Park
Sedalia
8.0 out of 10, Very good, (1 review)
"This is a lovely, spacious home in a great neighborhood. The location is great. It is across the street from a beautiful well-kept park with lots to do!"
United States
Nicki T.
The price is NZ$578
includes taxes & fees
24 Aug - 25 Aug
Walk to State Fairgrounds & Katy Trail, 4BR Home by Park

3. Peaceful Woodland Retreat - Spacious Home on 5 Acres

Peaceful Woodland Retreat - Spacious Home on 5 Acres
Sedalia
The price is NZ$536
includes taxes & fees
19 Aug - 20 Aug
Peaceful Woodland Retreat - Spacious Home on 5 Acres

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 NZ$215
includes taxes & fees
17 Aug - 18 Aug
Red cabin close to University of Central Missouri and Whiteman AF Base

5. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (21 reviews)
"Nice place to stay "
United States
Sam
The price is NZ$178
includes taxes & fees
17 Aug - 18 Aug
Hickory Hollow Resort

6. 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, (4 reviews)
"I've stayed here twice and will stay again. The owners are friendly and insightful. The property and cabins are very clean."
United States
Sylvia M.
The price is NZ$215
includes taxes & fees
17 Aug - 18 Aug
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

7. 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, (17 reviews)
"Excellent stay"
United States
Michael E.
The price is NZ$287
includes taxes & fees
17 Aug - 18 Aug
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

8. 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 NZ$215
includes taxes & fees
18 Aug - 19 Aug
Unit B Country home apartment near Warrensburg

9. 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
9.6 out of 10, Exceptional, (34 reviews)
"This house was so cute. It was on a dead end street and was very quiet. It was easy to access and was a good central spot while I was in Clinton visiting family. Would definitely stay here again."
United States
Cailyn
The price is NZ$298
includes taxes & fees
19 Aug - 20 Aug
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

10. Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
The price is NZ$215
includes taxes & fees
14 Sept - 15 Sept
Cute Little Cabin #3

11. 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 NZ$233
includes taxes & fees
17 Aug - 18 Aug
Green cabin close to University of Central Missouri and Whiteman AF Base

12. 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 NZ$306
includes taxes & fees
8 Sept - 9 Sept
The Bungalow at WAFB/Knob Noster pet friendly

13. Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (37 reviews)
"Awesome place to stay in Sedalia, beautiful cosy home. Top notch host. Would definitely recommend and stay again."
Canada
James
The price is NZ$327
includes taxes & fees
25 Aug - 26 Aug
Haven House New Comfortable and Clean Retreat

14. Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (46 reviews)
"Place was excellent!!"
United States
Garrett
The price is NZ$348
includes taxes & fees
25 Aug - 26 Aug
Home Away From Home

15. 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 NZ$251
includes taxes & fees
25 Aug - 26 Aug
Tan cabin close to University of Central Missouri and Whiteman AF Base

16. 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 NZ$268
includes taxes & fees
17 Aug - 18 Aug
Cabin 3 - Reel and Trigger

17. 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, (48 reviews)
"Perfect getaway to relax. We enjoyed our trip and will be booking again!"
United States
Cynthia M.
The price is NZ$386
includes taxes & fees
17 Aug - 18 Aug
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

18. 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 NZ$322
includes taxes & fees
23 Aug - 24 Aug
Downtown Retreat with large privacy fenced yard. Pet Friendly!

19. Fisher House Spacious Home in Tiny Home Village

Fisher House Spacious Home in Tiny Home Village
Sedalia
10.0 out of 10, Exceptional, (34 reviews)
"Can’t wait to stay again"
United States
Caleb B.
The price is NZ$327
includes taxes & fees
24 Aug - 25 Aug
Fisher House Spacious Home in Tiny Home Village

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, (10 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 NZ$351
includes taxes & fees
17 Aug - 18 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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?

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown: This holiday home rental outside of Windsor is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. 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 Clinton Community Center.

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.