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Windsor Cottage Rentals & Holiday Homes

Find the best cottages in Windsor - We found 61 exact matches

About Windsor Cottage Rentals on Casai.com

Searching for cottages to rent near Windsor? Casai features more than 61 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Windsor have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Casai’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Windsor.

Are you planning to travel to the lakeside, beach, or mountain area? Casai’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Casai boasts of 61 holiday cottages and places to stay in Windsor. The site provides unique Airbnb, VRBO, Casai-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

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Frequently Asked Questions About Windsor Rental Cottages

There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windsor:

The average cost for a cottage rental in Windsor is $264 per night. Casai has a wide list of great cottages near Windsor that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Windsor that allow you to bring your pet:

See all pet-friendly vacation rentals in Windsor on Casai.com

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windsor to find one that works for you.
As of 2026, the data from Casai.com shows that there are Over 61 private swimming pools or cottages with indoor pools in the Windsor area along with other great amenities.
About 61 cottages in Windsor boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Windsor on Casai.com
Yes, there are luxury cottages in Windsor. Find more luxury, lakefront, winter, & last-minute cottage rentals near Windsor.