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  4. Downtown
  5. Holiday Homes

196+ Downtown Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Downtown

Discover more than 196 holiday rentals in Downtown. PickleTrip™ holiday homes has everything you need to find a place to stay near Downtown, IL.

Whether you are looking for luxury villas in Downtown, 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 with private pickleball courts or nearby facilities. 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 Downtown with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Downtown for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Downtown with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Downtown Holiday Rentals

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

There are many holiday rentals available in Downtown; however, here are a few of the most popular holiday homes listed in Downtown on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Downtown to find one that works for you.
Yes, there are 196 self-catering family homes and holiday rentals in Downtown.
There are more than 196 luxury holiday homes in or near Downtown, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 196 pet friendly rentals that are available in Downtown.