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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windsor holiday rentals

A kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and a window with curtains.

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)
"Staying here at the start of a Katy trail bike trip. Stones throw from the trail and perfect house for the overnight. Host super friendly and helpful."
United States
Paul S.
The price is HK$981
HK$1,469 total
includes taxes & fees
4 Nov - 5 Nov
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
A row of cabins with wooden decks and stairs leading to the entrance.

2. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (26 reviews)
"Nice place to stay "
United States
Sam
The price is HK$699
HK$824 total
includes taxes & fees
29 Nov - 30 Nov
Hickory Hollow Resort
A cozy cabin interior with a kitchen, dining area, and a sofa.

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, (33 reviews)
"Clean, great communication, and a wonderful spot to stay. Will definitely return."
United States
Kelly
The price is HK$777
HK$929 total
includes taxes & fees
2 Nov - 3 Nov
Red cabin close to University of Central Missouri and Whiteman AF Base
Private kitchen

4. 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)
"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 HK$777
HK$929 total
includes taxes & fees
2 Nov - 3 Nov
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.
A spacious loft-style room with a wooden interior, a staircase, a sofa, and a television.

5. 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 HK$1,090
HK$1,266 total
includes taxes & fees
2 Nov - 3 Nov
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.

6. 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 HK$777
HK$929 total
includes taxes & fees
2 Nov - 3 Nov
Unit B Country home apartment near Warrensburg
A cozy cabin interior with a wooden staircase, a sofa, a chair, a kitchen area, and a clock on the wall.

7. 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 HK$1,090
HK$1,266 total
includes taxes & fees
2 Nov - 3 Nov
White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island.

8. 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.
Haven House New Comfortable and Clean Retreat
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, (21 reviews)
"Immaculate and lovely, check-in was super easy and location perfect."
United States
Sabrina D.
The price is HK$855
HK$1,013 total
includes taxes & fees
2 Nov - 3 Nov
Green cabin close to University of Central Missouri and Whiteman AF Base
A wooden cabin interior with a kitchen, dining area, and a ceiling fan.

10. 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 HK$934
HK$1,097 total
includes taxes & fees
2 Nov - 3 Nov
Unit A Country house near Warrensburg
A hallway with a wooden panel, a mirror, a door with frosted glass panels, and a ceiling light fixture.

11. Modern 2BR Townhome near the MO State Fair

Modern 2BR Townhome near the MO State Fair
Sedalia
The price is HK$1,038
HK$1,840 total
includes taxes & fees
12 Nov - 13 Nov
Modern 2BR Townhome near the MO State Fair
A two-story house with a stone facade, a number '2713' above the door, and a well-maintained lawn.

12. 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 HK$1,247
HK$1,403 total
includes taxes & fees
17 Nov - 18 Nov
Fisher House Spacious Home in Tiny Home Village
A kitchen with wooden cabinets, a microwave, an oven, and a dishwasher.

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

Walk to State Fairgrounds & Katy Trail, 4BR Home by Park
Sedalia
9.6 out of 10, Exceptional, (8 reviews)
The price is HK$1,404
HK$2,390 total
includes taxes & fees
30 Nov - 1 Dec
Walk to State Fairgrounds & Katy Trail, 4BR Home by Park
A two-story wooden house with a covered porch and a flagpole.

14. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
3.0 star property
Clinton
The price is HK$1,326
HK$4,035 total
includes taxes & fees
25 Nov - 26 Nov
Truman Lake Retreat: Relax and Unwind
A living room with a fireplace, a television mounted above it, and a patterned rug on the floor.

15. 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, (14 reviews)
"Great property and a really good location. Very responsive host!"
United States
Jo H.
The price is HK$1,012
HK$1,560 total
includes taxes & fees
29 Nov - 30 Nov
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat
A two-story wooden building with a covered porch and a garage.

16. Eagle's Nest - Reel and Trigger

Eagle's Nest - Reel and Trigger
Tom Township
9.0 out of 10, Wonderful, (2 reviews)
"Kinda small but served the purpose for us guys"
United States
Gary A.
The price is HK$1,469
HK$1,639 total
includes taxes & fees
2 Nov - 3 Nov
Eagle's Nest - Reel and Trigger
A spacious dining area with a high ceiling fan, a kitchen with wooden cabinets, and a large window providing natural light.

17. Katy Trail Rest Stop

Katy Trail Rest Stop
Sedalia
9.4 out of 10, Exceptional, (53 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 HK$1,451
HK$2,146 total
includes taxes & fees
5 Nov - 6 Nov
Katy Trail Rest Stop
A two-story wooden house with a covered porch and a flagpole.

18. 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.
Truman Lake Retreat: Relax and Unwind
A kitchen with white cabinets, a marble countertop, a coffee maker, and a kettle.

19. King Beds_Cozy 2BR Home_Sleeps 5_Warrensburg

King Beds_Cozy 2BR Home_Sleeps 5_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 HK$932
HK$3,419 total
includes taxes & fees
2 Nov - 3 Nov
King Beds_Cozy 2BR Home_Sleeps 5_Warrensburg
A kitchen with wooden cabinets, a black refrigerator, a white microwave, a white refrigerator, a sink, and a bar stool area.

20. The Lodge - Large Rental

The Lodge - Large Rental
Tom Township
10.0 out of 10, Exceptional, (1 review)
"Had 10 people in the house plenty of room will definitely be staying there again"
United States
Skyler M.
The price is HK$2,728
HK$3,900 total
includes taxes & fees
2 Nov - 3 Nov
The Lodge - Large Rental
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

Fairfield Inn & Suites by Marriott Warrensburg

Fairfield Inn & Suites by Marriott Warrensburg

10/10 Excellent
"Nice clean place, shower is really nice and people are super nice."
angela 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Warrensburg

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
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  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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.