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 reviews)
"Perfect stop right on the Katy Trail! All was just as described in the listing. Close to shopping areas to stock up on food and supplies. Sent stay request on Friday after 6pm to arrive on Saturday and host replied within an hour that late reservation was no problem and property would be ready for my stay. "
United States
Pat K.
The price is NZ$313
includes taxes & fees
9 Feb - 10 Feb
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, (23 reviews)
"Clean and comfortable stay"
United States
David F.
The price is NZ$193
includes taxes & fees
5 Mar - 6 Mar
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.
Warrensburg
10.0 out of 10, Exceptional, (1 review)
"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 NZ$182
includes taxes & fees
5 Feb - 6 Feb
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

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 reviews)
"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 NZ$263
includes taxes & fees
23 Feb - 24 Feb
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.2 out of 10, Wonderful, (56 reviews)
"Very gracious host!"
United States
rachell c.
The price is NZ$300
includes taxes & fees
5 Feb - 6 Feb
Cozy Home w/ Doggy Fence

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, (46 reviews)
"We love staying here for the great location to UCM and the wonderful downtown area. "
United States
Michelle G.
The price is NZ$255
includes taxes & fees
16 Feb - 17 Feb
Downtown Retreat with large privacy fenced yard. Pet Friendly!

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, (24 reviews)
"Great place to stay! "
United States
Keith H.
The price is NZ$264
includes taxes & fees
5 Feb - 6 Feb
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

Candlestick Suite

Candlestick Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Comfortable stay"
United States
David F.
The price is NZ$295
includes taxes & fees
18 Feb - 19 Feb
Candlestick Suite

Cozy 2BR_Near UCM_King_Beds|Family Friendly

Cozy 2BR_Near UCM_King_Beds|Family Friendly
Warrensburg
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay here and would definitely recommend for couples or small families."
United States
Richard W.
Cozy 2BR_Near UCM_King_Beds|Family Friendly

Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade

Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade
Warsaw
10.0 out of 10, Exceptional, (6 reviews)
"We wanted a place close to the lake and this was perfect. Super clean and just a beautiful layout all around. The neighborhood felt safe and friendly. I wouldn't look any further if im planning another trip to the area as i will check with this place first "
United States
Christopher E.
Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade

Peacock Suite

Peacock Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (3 reviews)
"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 NZ$304
includes taxes & fees
18 Feb - 19 Feb
Peacock Suite

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 reviews)
"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 NZ$484
includes taxes & fees
5 Feb - 6 Feb
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews

Unit A Country house near Warrensburg

Unit A Country house near Warrensburg
Warrensburg
10.0 out of 10, Exceptional, (2 reviews)
"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 NZ$227
includes taxes & fees
8 Feb - 9 Feb
Unit A Country house near Warrensburg

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 reviews)
"Very nice little place. Perfect place to stay for a fishing trip on Truman Lake. "
United States
Caleb T.
The price is NZ$499
includes taxes & fees
5 Feb - 6 Feb
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

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 review)
"Very peaceful area.. overnight stay.. convenient to everything.. highly recommend "
United States
David J.
The price is NZ$499
includes taxes & fees
5 Feb - 6 Feb
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay!!!"
United States
Lynn W.
The price is NZ$288
includes taxes & fees
17 Feb - 18 Feb
Home Away From Home

Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps

Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps
Warsaw
10.0 out of 10, Exceptional, (4 reviews)
"The house was very clean! "
United States
brandon a.
The price is NZ$408
includes taxes & fees
4 Mar - 5 Mar
Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps

Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.4 out of 10, Exceptional, (47 reviews)
"Work crew stayed here during an out of town project. They were very happy with the accomodations and commented how much nicer and spacious this stay was over a hotel room.The host was great to work with, I would definately book again for a work trip, or even for a family getaway to Sedalia."
United States
Shadyia W.
The price is NZ$361
includes taxes & fees
18 Feb - 19 Feb
Katy Trail Rest Stop

Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (24 reviews)
"Very easy check-in and very clean. It was a great location and we enjoyed our stay."
United States
Chad H.
The price is NZ$259
includes taxes & fees
9 Feb - 10 Feb
Haven House New Comfortable and Clean Retreat

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.6 out of 10, Excellent, (14 reviews)
"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 NZ$174
includes taxes & fees
5 Mar - 6 Mar
Hickory Hollow Resort
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 favorite 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 depends 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 NZ$193 per night. Entering your travel dates in the search wizard you might find 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.