Windsor cottage rentals

We found 30 cottage rentals — enter your dates for availability

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a cottage rental in Windsor?
Upscale or budget, in a popular tourist area or a little further out, peak season or quiet season — these factors and more will determine how much your cottage rental in Windsor will cost. The length of your trip can also affect the overall price. Some holiday rentals offer discounts for longer bookings, so keep your eyes peeled for special offers.
When is the best time to rent a cottage in Windsor?
With temperatures ranging from 19ºC to 26ºC, August is when most people book a cottage rental in Windsor. Given it's the busiest time of year, try to plan ahead and secure your stay. Or, explore the off-season for a more relaxing Southwestern Ontario retreat.
Where can I rent a Windsor holiday cottage with great views?
When looking for your cottage rental in Windsor, make use of our "Location" filter. This lets you choose the types of areas you want to stay in, whether that's around nature or somewhere more central.
Does Windsor have any lakeside cottages?
Gorgeous views of glittering water, the beauty of nature and outdoor activities are some of the things to enjoy in one of Stayz's lakeside cottage rentals. Use our handy "Location" filter and click on "Lake" to find out if there are any cosy retreats in Windsor near the water.
What are the top things to do in Windsor?
It's easy to see why families love Windsor, with top attractions like Adventure Bay Family Water Park, Ambassador Bridge and Devonshire Mall to explore. Check out this destination's wonders together and then return to the comforts of your cottage rental.
Why should I book my holiday cottage with Stayz?
No sharing your space, no awkward small talk with people you don't know. When you book a Stayz cottage rental, you get the whole place all to yourself. Need to cancel or amend your travel plans? Our flexible cancellation policies mean you're able to book your cottage with peace of mind.