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Windsor Vacation Rentals

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Our top choices for Windsor vacation 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, (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 CA $175
CA $260 total
includes taxes & fees
Nov 8 - Nov 9
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

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 CA $138
CA $162 total
includes taxes & fees
Nov 14 - Nov 15
Hickory Hollow Resort

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 CA $138
CA $166 total
includes taxes & fees
Nov 8 - Nov 9
Red cabin close to University of Central Missouri and Whiteman AF Base

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 CA $138
CA $166 total
includes taxes & fees
Nov 9 - Nov 10
Delightful Cabin #4 close to Warrensburg, Knob Knoster, and Clinton.

5. Cute Little Cabin #3

Cute Little Cabin #3
warrensburg
10.0 out of 10, Exceptional, (1 review)
"This was a very nice cabin, it was clean and had everything we needed for the stay."
United States
Anthony
The price is CA $138
CA $166 total
includes taxes & fees
Dec 4 - Dec 5
Cute Little Cabin #3

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

Cozy 1-bedroom Cabin 4C in serene Warrebsburg with AC
`Warrebsburg
The price is CA $138
CA $166 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1-bedroom Cabin 4C in serene Warrebsburg with AC

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 CA $138
CA $166 total
includes taxes & fees
Nov 8 - Nov 9
Unit B Country home apartment near Warrensburg

8. 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 CA $194
CA $226 total
includes taxes & fees
Nov 12 - Nov 13
Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

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 CA $152
CA $181 total
includes taxes & fees
Nov 8 - Nov 9
Green cabin close to University of Central Missouri and Whiteman AF Base

10. 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 CA $194
CA $226 total
includes taxes & fees
Nov 17 - Nov 18
White cabin in the woods close to Univ. of Central Missouri and Whiteman AF Base

11. 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 CA $166
CA $196 total
includes taxes & fees
Nov 5 - Nov 6
Unit A Country house near Warrensburg

12. Modern 2BR Townhome near the MO State Fair

Modern 2BR Townhome near the MO State Fair
Sedalia
The price is CA $176
CA $307 total
includes taxes & fees
Nov 30 - Dec 1
Modern 2BR Townhome near the MO State Fair

13. Cabin 2 - Reel and Trigger

Cabin 2 - Reel and Trigger
Tom Township
The price is CA $187
CA $209 total
includes taxes & fees
Nov 5 - Nov 6
Cabin 2 - Reel and Trigger

14. 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 CA $180
CA $279 total
includes taxes & fees
Nov 17 - Nov 18
Blind Boone Bungalow in the 'Burg– Charming and Stylish 2BR Downtown Retreat

15. 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 CA $166
CA $610 total
includes taxes & fees
Nov 5 - Nov 6
King Beds_Cozy 2BR Home_Sleeps 5_Warrensburg

16. 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 CA $222
CA $261 total
includes taxes & fees
Nov 16 - Nov 17
Fisher House Spacious Home in Tiny Home Village

17. 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 CA $176
CA $695 total
includes taxes & fees
Nov 25 - Nov 26
Truman Lake Retreat: Relax and Unwind

18. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
3.0 star property
Clinton
The price is CA $237
CA $720 total
includes taxes & fees
Nov 25 - Nov 26
Truman Lake Retreat: Relax and Unwind

19. 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 CA $87
CA $312 total
includes taxes & fees
Nov 5 - Nov 6
The Gallery - Modern Loft Apartment

20. Candlestick Suite

Candlestick Suite
Sedalia Downtown Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Loved the charm of this historic building! Beautifully cared for and the suite was lovely :) The balcony was a great spot to watch the fireworks and we walked to some great places for drinks and pizza. Highly recommend!"
United States
Melissa O.
The price is CA $172
CA $250 total
includes taxes & fees
Nov 5 - Nov 6
Candlestick Suite
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we offer vacation rentals near top points of interest in Windsor, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Windsor?

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.: This vacation home rental outside of Windsor is located on a lake and has a patio, a barbecue grill, 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 larger area, you’ll find Whiteman Air Force Base and Harry S. Truman State Park.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Windsor. Vacation rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family getaway.