Windsor Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windsor holiday rentals

A living room with a dark-colored sofa, a small table, a ceiling fan, a potted plant, and a door with a stained glass window.

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)
"Super tidy and homey little place to stay! The communication was superb, would highly recommend staying there."
United States
Samantha D.
The price is NZ$337
includes taxes & fees
22 Nov - 23 Nov
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
A swimming pool with white lounge chairs and a wooden fence in the background.

2. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (27 reviews)
"Nice place to stay "
United States
Sam
The price is NZ$209
includes taxes & fees
15 Nov - 16 Nov
Hickory Hollow Resort
A red metal shed with a white door and window, a small porch, and gravel ground.

3. 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, (34 reviews)
"Clean, great communication, and a wonderful spot to stay. Will definitely return."
United States
Kelly
The price is NZ$200
includes taxes & fees
16 Nov - 17 Nov
Red cabin close to University of Central Missouri and Whiteman AF Base
A spacious loft-style room with a wooden interior, a staircase, a sofa, and a television.

4. 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 NZ$292
includes taxes & fees
15 Nov - 16 Nov
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri
A small, dark-colored cabin with a porch, two Adirondack chairs, and a grill.

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

Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Warrensburg
9.8 out of 10, Exceptional, (7 reviews)
"Great place to stay- would stay again if ever back in town."
United States
Brad M.
The price is NZ$214
includes taxes & fees
16 Nov - 17 Nov
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
Private kitchen

6. Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
9.0 out of 10, Wonderful, (2 reviews)
"This was a very nice cabin, it was clean and had everything we needed for the stay."
United States
Anthony
The price is NZ$214
includes taxes & fees
7 Dec - 8 Dec
Cute Little Cabin #3
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
8.8 out of 10, Excellent, (6 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$214
includes taxes & fees
17 Nov - 18 Nov
Unit B Country home apartment near Warrensburg
A small, dark-colored cabin with a porch, two Adirondack chairs, and a grill.

8. Cozy 1-bedroom Cabin 4C in serene Warrebsburg with AC

Cozy 1-bedroom Cabin 4C in serene Warrebsburg with AC
`Warrebsburg
10.0 out of 10, Exceptional, (1 review)
"It was great all around. The location outside of the city, the host is great to talk with, the cabin was comfortable and had everything I needed. Best place all around!"
United States
Aaron H.
The price is NZ$200
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom Cabin 4C in serene Warrebsburg with AC
A cozy cabin interior with a wooden staircase, a sofa, a chair, a kitchen area, and a clock on the wall.

9. White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base

White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base
Warrensburg
9.4 out of 10, Exceptional, (16 reviews)
"This is the best place"
United States
Sergio A.
The price is NZ$279
includes taxes & fees
16 Nov - 17 Nov
White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base
A cozy cabin interior with a wooden staircase, a sofa, a chair, and a refrigerator.

10. 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, (21 reviews)
"Immaculate and lovely, check-in was super easy and location perfect."
United States
Sabrina D.
The price is NZ$234
includes taxes & fees
15 Nov - 16 Nov
Green cabin close to University of Central Missouri and Whiteman AF Base
A covered patio area with a grill, table, chairs, and string lights.

11. Haven House New Comfortable and Clean Retreat

Haven House New Comfortable and Clean Retreat
Sedalia
10.0 out of 10, Exceptional, (41 reviews)
"Our favorite place to stay in Sedalia!"
United States
Cara T.
The price is NZ$335
includes taxes & fees
5 Dec - 6 Dec
Haven House New Comfortable and Clean Retreat
A wooden cabin interior with a kitchen, dining area, and a ceiling fan.

12. Unit A Country house near Warrensburg

Unit A Country house near Warrensburg
Warrensburg
9.6 out of 10, Exceptional, (5 reviews)
"Everything was exactly as described and the owner was a great host."
United States
leslie f.
The price is NZ$241
includes taxes & fees
16 Nov - 17 Nov
Unit A Country house near Warrensburg
A two-story house with a stone facade, a number '2713' above the door, and a well-maintained lawn.

13. Fisher House Spacious Home in Tiny Home Village

Fisher House Spacious Home in Tiny Home Village
Sedalia
10.0 out of 10, Exceptional, (41 reviews)
"Can’t wait to stay again"
United States
Caleb B.
The price is NZ$335
includes taxes & fees
16 Nov - 17 Nov
Fisher House Spacious Home in Tiny Home Village
A hallway with a wooden panel, a mirror, a door with frosted glass panels, and a ceiling light fixture.

14. Modern 2BR Townhome near the MO State Fair

Modern 2BR Townhome near the MO State Fair
Sedalia
The price is NZ$389
includes taxes & fees
16 Nov - 17 Nov
Modern 2BR Townhome near the MO State Fair
A modern apartment with a kitchen, living room, and dining area.

15. Scarlet Suite

Scarlet Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Great place "
United States
Francisco M.
The price is NZ$380
includes taxes & fees
15 Nov - 16 Nov
Scarlet Suite
A beige two-story house with a front porch, a mailbox, and a door with a wreath.

16. 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, (15 reviews)
"Really cute property, comfortable stay. Just what we needed as a family of 4. Mattress is on the firmer side but we did not mind at all and slept well."
United States
Kathleen
The price is NZ$345
includes taxes & fees
16 Nov - 17 Nov
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
A compact kitchen with wooden cabinets, a white refrigerator, a stove, and a sink.

17. 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$270
includes taxes & fees
23 Nov - 24 Nov
Cabin 3 - Reel and Trigger
A kitchen with white cabinets, a marble countertop, a coffee maker, and a kettle.

18. Cozy 2BR Home_Sleeps 5_KingBeds_In Warrensburg

Cozy 2BR Home_Sleeps 5_KingBeds_In Warrensburg
Warrensburg
9.4 out of 10, Exceptional, (6 reviews)
"We really enjoyed our stay here and would definitely recommend for couples or small families."
United States
Richard W.
The price is NZ$818
includes taxes & fees
15 Nov - 16 Nov
Cozy 2BR Home_Sleeps 5_KingBeds_In Warrensburg
A covered patio with wooden benches and chairs, a view of a lake, and potted plants.

19. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
Clinton
10.0 out of 10, Exceptional, (15 reviews)
"A very nice place to stay that was conveniently located to where we spent most of our time."
United States
Jason S.
The price is NZ$878
includes taxes & fees
25 Nov - 26 Nov
Truman Lake Retreat: Relax and Unwind
A kitchen with wooden cabinets, a microwave, and a sink.

20. The Gallery - Modern Loft Apartment

The Gallery - Modern Loft Apartment
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (1 review)
"It was great for the state fair within 2 miles but far enough away it was calm and quite"
United States
Christy M.
The price is NZ$376
includes taxes & fees
15 Nov - 16 Nov
The Gallery - Modern Loft Apartment
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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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$199 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?

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 Harry S. Truman 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.