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, (34 reviews)
"Great property for my stay for business in Leeton …would definitely stay here again !"
United States
Diane D.
The price is NZ$326
includes taxes & fees
8 May - 9 May
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (60 reviews)
"We enjoyed our stay this was our second time look forward to doing again. "
United States
Gloria G.
The price is NZ$303
includes taxes & fees
10 May - 11 May
Cozy Home w/ Doggy Fence

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, (25 reviews)
"These places are amazing. Simple, but clean, and well Maintained. Great value for the money."
United States
Anthony
The price is NZ$212
includes taxes & fees
10 May - 11 May
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, (2 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 NZ$212
includes taxes & fees
11 May - 12 May
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points
Osceola
10.0 out of 10, Exceptional, (1 review)
"Very quiet and peaceful. The interior was clean and updated. Nice living room with 3 love seats, which I think are also pull-out beds? And there is a card table with sturdy comfortable chairs that can seat maybe 6 people. There is a small, but very nice kitchen. Two bathrooms, each attached to its own bathroom, with the bathrooms also having a second door opening to the living room for convenience. Beds were comfortable, but just note for guests who are bigger or have mobility issues, the beds...
United States
Douglas H.
The price is NZ$247
includes taxes & fees
11 May - 12 May
Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

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, (28 reviews)
"Perfect place to stay during a weekend family visit!"
United States
Terry M.
The price is NZ$286
includes taxes & fees
10 May - 11 May
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

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, (46 reviews)
"Beautiful had everything we needed and was very peaceful "
United States
Raelynn W.
The price is NZ$451
includes taxes & fees
10 May - 11 May
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Home Away From Home

Home Away From Home
Warrensburg
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay!!!"
United States
Lynn W.
The price is NZ$303
includes taxes & fees
10 May - 11 May
Home Away From Home

Cabin 10 - Reel and Trigger

Cabin 10 - Reel and Trigger
Tom Township
10.0 out of 10, Exceptional, (1 review)
"We had family camping at the state park for the long weekend and wanted to stay close by. The cabin was perfect. We had time to visit easily and also an air conditioned place to sleep in. It also is dog friendly so we were able to bring the dogs. Getting a dog sitter on a long weekend is difficult. "
United States
Audrey B.
The price is NZ$265
includes taxes & fees
10 May - 11 May
Cabin 10 - Reel and Trigger

The Bungalow at WAFB/Knob Noster pet friendly

The Bungalow at WAFB/Knob Noster pet friendly
Knob Noster
10.0 out of 10, Exceptional, (16 reviews)
"Awesome clean place many amenities Would stay there again. "
United States
Marcia G.
The price is NZ$266
includes taxes & fees
19 May - 20 May
The Bungalow at WAFB/Knob Noster pet friendly

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, (15 reviews)
"The cabin was beautiful! Nice, quiet and cozy! Will definitely stay there again!"
United States
Cassie
The price is NZ$284
includes taxes & fees
10 May - 11 May
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

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$302
includes taxes & fees
10 May - 11 May
Candlestick Suite

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, (52 reviews)
"Very nice place to stay! Only stayed for a few hours because we were just passing through, but the beds were very comfortable!"
United States
Zachary B.
The price is NZ$272
includes taxes & fees
20 May - 21 May
Downtown Retreat with large privacy fenced yard. Pet Friendly!

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (17 reviews)
"Nice place to stay "
United States
Sam
The price is NZ$147
includes taxes & fees
6 June - 7 June
Hickory Hollow Resort

Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.4 out of 10, Exceptional, (48 reviews)
"Everything was great."
United States
Calvin S.
The price is NZ$387
includes taxes & fees
10 May - 11 May
Katy Trail Rest Stop

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$310
includes taxes & fees
11 May - 12 May
Peacock Suite

Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
The price is NZ$212
includes taxes & fees
19 May - 20 May
Cute Little Cabin #3

Unit B Country home apartment near Warrensburg

Unit B Country home apartment near Warrensburg
Warrensburg
8.8 out of 10, Excellent, (3 reviews)
"Amazing experience! Clean and comfortable. Easy drive to UCM. We would definitely stay here again!"
United States
Jason
The price is NZ$212
includes taxes & fees
10 May - 11 May
Unit B Country home apartment near Warrensburg

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, (7 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.
The price is NZ$1,007
includes taxes & fees
19 May - 20 May
Lake House on Truman Lake|Sleeps10|Fire Pit_Arcade

Charming Micro Cabin 4 in the heart of the Ozarks

Charming Micro Cabin 4 in the heart of the Ozarks
Osceola
The price is NZ$165
includes taxes & fees
10 May - 11 May
Charming Micro Cabin 4 in the heart of the Ozarks
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$212 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?

Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.