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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Windsor vacation rentals

Basic Cabin, Resort View | Terrace/patio

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very Good, (20 reviews)
"Nice place to stay "
United States
Sam
$99 nightly
The price is $105
Aug 23 - Aug 24
Total with taxes and fees
Hickory Hollow Resort
House (5 Bedrooms) | Interior

Walk to Dtwn Warrensburg: Cozy Family Home!

Walk to Dtwn Warrensburg: Cozy Family Home!
3.0 star property
Warrensburg
$420 nightly
The price is $480
Aug 2 - Aug 3
Total with taxes and fees
Walk to Dtwn Warrensburg: Cozy Family Home!
House (4 Bedrooms) | Interior

Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
3.0 star property
Clinton
$469 nightly
The price is $514
Aug 13 - Aug 14
Total with taxes and fees
Truman Lake Retreat: Relax and Unwind
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

Westbridge Inn and Suites

Westbridge Inn and Suites

8/10 Good
"The best thing I liked about this was how close it was to the downtown area. It is located just on the edge of the city right off of the highway. Drug stores gas stations Banks and fast food restaurants are nearby and yet out of the way. The room I heard was one queen size bed which was not extremely hard so it made for a very comfortable sleep. There were even wonderfully soft pillows available. The breakfast was minimal. You were able to make waffles there was no eggs you were able to make biscuits and gravy there was no other meat. Except for this low breakfast because I now had to go and purchase it elsewhere, I would not mind staying here again because of the atmosphere and it's location. I stayed for a short period of time but this is some place I could stay for longer if I needed to. Give it a try, it's worth the price to do so."
A M 1-night trip
Posted 10 hours ago
Westbridge Inn and Suites

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 $126 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.

Explore a world of travel with Expedia

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?

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown: This vacation home rental outside of Windsor is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. 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.