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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windsor vacation rentals

A cozy tented room with a bed, a lamp, and a view of the outdoors.

1. Mi-Clos

Mi-Clos
2.0 star property
Orford
10.0 out of 10, Exceptional, (30 reviews)
"Amazing stay !"
Canada
Frederik
The price is CA $388
CA $446 total
includes taxes & fees
Oct 15 - Oct 16
Mi-Clos
A wooden cabin with a picnic table and a person standing by the window.

2. Station Chêne Rouge

Station Chêne Rouge
2.5 star property
Hatley
9.6 out of 10, Exceptional, (107 reviews)
"Great staff , well kept and clean property , exactly as advertised ! Loved being able to have our dog with us as well :) would definitely return ! So quiet and relaxing"
Canada
Kevin
The price is CA $107
CA $211 total
includes taxes & fees
Oct 15 - Oct 16
Station Chêne Rouge
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

Hotel Cheribourg, an Ascend Collection Hotel

Hotel Cheribourg, an Ascend Collection Hotel

10/10 Excellent
"A NICE PLACE I HAVE BEEN THERE FOUR TIMES."
mohamed 1-night trip
Posted 9 hours ago
Hotel Cheribourg, an Ascend Collection Hotel

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $211 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 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. 

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we give you a choice of vacation rentals near popular local attractions in Windsor, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Windsor has to offer?

Condo 2 Bedrooms Jardin des Sables: Visitors like this Windsor vacation home rental. It is located next to a golf course and has a fireplace, a private balcony, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

What’s there to see and do in Windsor?

While exploring the area, visit family-friendly sights like Multigolf Sherbrooke, or get outside and enjoy nature at Magog River Gorge. In the larger area, you’ll find le Parc Historique de la Poudriere de Windsor and Sherbrooke Exhibition Center.

What’s a vacation rental in Windsor like?

Vacation rentals are privately owned properties you can book for a long or short time in Windsor. Vacation rentals offer extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.