1. USA
  2. Illinois
  3. Chicago
  4. Crestwood
  5. Holiday Homes

155+ Crestwood Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Crestwood

Discover more than 155 holiday rentals in Crestwood. Rent By Owner holiday homes has everything you need to find a place to stay near Crestwood, IL.

Whether you are looking for luxury villas in Crestwood, 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 Crestwood with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Crestwood for families, large parties, or private owner accommodations for long or short trips. Crestwood Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Crestwood with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

Show more
Show less

Frequently Asked Questions About Crestwood Holiday Rentals

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

There are many holiday rentals available in Crestwood; however, here are a few of the most popular holiday homes listed in Crestwood 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 Crestwood to find one that works for you.
Yes, there are 155 self-catering family homes and holiday rentals in Crestwood.
There are more than 155 luxury holiday homes in or near Crestwood, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: