156+ O'Brien Field Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near O'Brien Field

Discover more than 156 holiday rentals in O'Brien Field. PickleTrip™ holiday homes has everything you need to find a place to stay near O'Brien Field, IL.

Whether you are looking for luxury villas in O'Brien Field, 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 O'Brien Field with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in O'Brien Field 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 O'Brien Field with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About O'Brien Field Holiday Rentals

There are a lot of options in O'Brien Field. If you plan on staying in the O'Brien Field 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 O'Brien Field:

There are many holiday rentals available in O'Brien Field; however, here are a few of the most popular holiday homes listed in O'Brien Field on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in O'Brien Field to find one that works for you.
Yes, there are 156 self-catering family homes and holiday rentals in O'Brien Field.
There are more than 156 luxury holiday homes in or near O'Brien Field, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 156 pet friendly rentals that are available in O'Brien Field.