Windsor Vacation Rentals from $105: Search Short-Term 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

Windsor

Paul S.

$181 nightly

Sep 21 - Sep 22

Total with taxes and fees

2. Red cabin close to University of Central Missouri and Whiteman AF Base

Warrensburg

Kelly G.

$119 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Warrensburg

Melanie

$119 nightly

Sep 21 - Sep 22

Total with taxes and fees

Basic Cabin, Resort View | Terrace/patio

4. Hickory Hollow Resort

Clinton

Sam

$99 nightly

Oct 20 - Oct 21

Total with taxes and fees

5. Cute Little Cabin #3

warrensburg

$119 nightly

Sep 21 - Sep 22

Total with taxes and fees

6. Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

Warrensburg

Michael E.

$159 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

`Warrebsburg

$119 nightly

Sep 21 - Sep 22

Total with taxes and fees

8. Unit B Country home apartment near Warrensburg

Warrensburg

Mary K H.

$119 nightly

Sep 22 - Sep 23

Total with taxes and fees

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Top Windsor Hotel Reviews

Residential Suites Warrensburg by Hotel O US 50

10/10 Excellent

"Hotel currently going through chain changes and updating property. So maintenence and under construction currently should not be a reflection. Amenities are limited to what is publicly available. No pool, continental breakfast but they compensate with price and cleanliness and staff professionalism."

Best Western State Fair Inn

8/10 Good

"The room was very old and tatty looking. The beds were noisy and extremely hard the bathroom was so small you had to contort your body to get the door closed without falling into the toilet. Outside the grass was long and unkempt with trash such as bottles and bottle tops all over the place. The breakfast was excellent hence the overall four stars."

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

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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.

Windsor Vacation Rentals

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Check prices for these dates

Our top choices for Windsor vacation rentals

1. Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO

2. Red cabin close to University of Central Missouri and Whiteman AF Base

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

4. Hickory Hollow Resort

5. Cute Little Cabin #3

6. Blue Cabin in the woods close to Whiteman AF Base and Univ. of Central Missouri

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

8. Unit B Country home apartment near Warrensburg

9. Downtown Retreat with large privacy fenced yard. Pet Friendly!

10. The Bungalow at WAFB/Knob Noster pet friendly

11. Green cabin close to University of Central Missouri and Whiteman AF Base

12. Cozy Home w/ Doggy Fence

13. Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews

14. Home Away From Home

15. Haven House New Comfortable and Clean Retreat

16. Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

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

18. Cabin 1 - Reel and Trigger

19. The Gallery - Modern Loft Apartment

20. Tan cabin close to University of Central Missouri and Whiteman AF Base

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Residential Suites Warrensburg by Hotel O US 50

Find out more about Windsor

Explore a world of travel with Expedia

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