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72+ New Windsor Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near New Windsor

Discover more than 72 holiday rentals in New Windsor. Rent By Owner holiday homes has everything you need to find a place to stay near New Windsor, IL.

Whether you are looking for luxury villas in New Windsor, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation 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 New Windsor with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in New Windsor for families, large parties, or private owner accommodations for long or short trips. New Windsor Pet-friendly holiday rentals are available. Book your favorite vacation rentals in New Windsor with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About New Windsor Holiday Rentals

There are a lot of options in New Windsor. If you plan on staying in the New 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 New Windsor:

There are many holiday rentals available in New Windsor; however, here are a few of the most popular holiday homes listed in New Windsor on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in New Windsor to find one that works for you.
Yes, there are 72 self-catering family homes and holiday rentals in New Windsor.
There are more than 72 luxury holiday homes in or near New Windsor, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: