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Northwest Side lake rentals

We found 222 lake rentals — enter your dates for availability

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    Enjoy full kitchens, laundry, pools, gardens and more

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Frequently asked questions

Are there any lake house holiday homes with a private pool in Northwest Side?
The only thing more appealing than a lake house is one with a private pool. Here are a few top-rated holiday homes in Northwest Side where memories are made by the water:

  • Catch up on some "me time" at "Luxury Loyola 3 Bedroom, 2 Bath", where the first item on your to-do list should be hanging out poolside or lakeside. It's located in Rogers Park and comes with family-friendly amenities, including a stovetop and a kitchen.
  • Also check out "Wrigleyville | Chicago Guest House | Not Just A Holiday Holiday home" in North Side. It features a kitchen and nearby museums, in addition to a swimming space that's all your own.

How can I find the best waterfront cabin holiday homes in Northwest Side?
Simply enter your desired travel dates, then use the filter tool to refine your search by property type, price and more. We appreciate that flexibility is important, which is why you can also find getaways that allow you to cancel for free. Whether it's a lakeside resort with room aplenty or a charming little place in the woods, we'll help you locate the best waterfront cabin holiday home.
How can I find cheap lake house holiday homes in Northwest Side?
It's a piece of cake. All you have to do is enter your preferred dates and destination, then use our filter tool to narrow your results by price. You can customize your search by property type, room count and more. With our Book with Confidence Guarantee, and our all-round amazing prices, your lakeside holiday doesn't need to be expensive.
What are some of the best lake houses to rent for a weekend in Northwest Side?
A lakeside escape is the ideal opportunity to take a breather and connect with nature. If you're in the mood to spend a few days near the water, browse these lake houses to rent for a weekend in or near Northwest Side:

  • Zip off to "Luxury Loyola 3 Bedroom, 2 Bath" and enjoy refreshing walks by the lake. When you want to sightsee, popular attractions including Wrigley Field and Northwestern University are within a short drive.
  • "Wrigleyville | Chicago Guest House | Not Just A Holiday Holiday home" is another enticing option. Consider adding Willis Tower and Art Institute of Chicago to your list if you spend your weekend here.