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236+ Windsor Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windsor

Discover more than 236 holiday rentals in Windsor. Casai holiday homes have everything you need to find a place to stay near Windsor, MA.

Whether you are looking for luxury villas in Windsor, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartments for family holidays, or stylish accommodations for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Windsor with a whole family or group, Casai holiday accommodations will make your trip memorable. We have plenty of places to stay in Windsor for families, large parties, or private owner accommodations for long or short trips. Windsor Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Windsor with Casai. Casai makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Windsor Holiday Rentals

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 Holiday Home Rentals in Windsor:

There are many holiday rentals available in Windsor; however, here are a few of the most popular holiday homes listed in Windsor on our website:
At Casai.com most of our places to stay are perfect for families. Check out the complete list of holiday homes in Windsor to find one that works for you.
Yes, there are 236 self-catering family homes and holiday rentals in Windsor.
There are more than 236 luxury holiday homes in or near Windsor, according to 2025 data from Casai.com. Consider these homes for your next holiday:
Yes, there are 236 pet friendly rentals that are available in Windsor.