South Side lake rentals

We found 205 lake rentals — enter your dates for availability

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Frequently asked questions

Can I find lakefront holiday homes in South Side?
With a lakefront holiday home you'll be ideally placed to experience one of Mother Nature's most stunning spectacles. Enjoy the tranquility of being near wilderness and water at one of these properties:

  • Map out a route to Greater Grand Crossing and spend a few days or longer at "3 Bedroom Apartment Easily 15 Mins From Downtown 10 Mins From Chicago's Beach". An ice maker and a hair dryer are among the conveniences you'll find at this lakeside holiday home.
  • After a happy day filled with exciting outdoor activities, kick back and relax at "The Woodlawn Oasis Is An Absolutely Beautiful Newly Rehabbed Apartment". This popular escape in Woodlawn provides guests with heating and cable/satellite TV services.

Are there any lake house holiday homes with a private pool in South Side?
Spend your holiday at a lake house holiday home with a private pool in South Side and submerge yourself in watery fun. Having a splashing good time will be your top priority at one of these impressive getaways:

  • The pool at "Luxury Loyola 3 Bedroom, 2 Bath" will add another layer of fun to your lakeside escape. Located in Rogers Park, this holiday home house also features an oven and a garden.
  • "Wrigleyville | Chicago Guest House | Not Just A Holiday Holiday home" in North Side is also a hit with guests. There's a whole lot to love about this retreat apart from its location and swimming space, such as nearby museums and a kitchen.

How can I find the best waterfront cabin holiday homes in South Side?
For the best waterfront cabin holiday homes around South Side, type in your preferred dates and use the available filter tool to fine-tune your search by location, price, property type and more. Make use of our map to find a great destination. Think your plans might change? Not a problem. Use the filter if you'd like cabin holiday homes that allow free cancellation. You won't have any difficulty finding a place for you to relax, laugh and connect with the people you love most.
How can I find cheap lake house holiday homes in South Side?
Locking in a cheap lake house holiday home on Bookabach is a cinch. Enter your preferred dates and destination, then use our handy filter tool to narrow your search by room count, price and more. Flexibility matters, so you'll be pleased to know that you can seek out holiday homes that also offer free cancellation. Our Book with Confidence Guarantee means you can enjoy a trouble-free holiday with Bookabach.
What are some of the best lake houses to rent for a weekend in South Side?
Get together with the family, relax, go on a trek — there are boatloads of lake houses to rent for a weekend in South Side where you can do all that and more. Here are two sought-after options to get you started:

  • Nestled in Greater Grand Crossing, you can pack a lot of fun into a short time at "3 Bedroom Apartment Easily 15 Mins From Downtown 10 Mins From Chicago's Beach". Get out and explore your lovely lakeside surroundings and then kick back and enjoy everything that's on offer at this popular retreat.
  • "The Woodlawn Oasis Is An Absolutely Beautiful Newly Rehabbed Apartment" in Woodlawn is another excellent option for a weekend getaway. Find some cool outdoor pursuits to do by the lake or just take it easy and do nothing.