What are the top rated Cottage Rentals in Chicago?

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Chicago: <a href="/property/lakefront-cottage-with-gorgeous-sunsets/HA-3213021839" class="class="static-page-link"">Lakefront Cottage with Gorgeous Sunsets</a> <a href="/property/4-the-cozy-cottage/HA-3213142920" class="class="static-page-link"">#4 The Cozy Cottage</a> <a href="/property/the-lodge-sweet-waterfront-cottage-separate-unit/HA-3212775723" class="class="static-page-link"">The Lodge, Sweet Waterfront Cottage, Separate Unit</a> <a href="/property/2-the-bluff-house-the-cottages-on-petite-lake/HA-3213142918" class="class="static-page-link"">#2 The Bluff House @ The Cottages on Petite Lake</a> <a href="/property/the-yellow-cottage-cottages-on-petite-lake/HA-3213142916" class="class="static-page-link"">The Yellow Cottage @ Cottages on Petite Lake</a> <a href="/property/lakehouse-getaway/HA-3214284547" class="class="static-page-link"">Lakehouse Getaway</a> <a href="/property/the-pleasant-hill-cottage-storybook-luxury-near-lake-michigan-heart-of-it-all/HA-3214752161" class="class="static-page-link"">The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan &amp; Heart Of It All!</a> <a href="/property/cottingham-cottage-peaceful-family-retreat-near-great-lakes-naval-base/HA-3214894225" class="class="static-page-link"">Cottingham Cottage – Peaceful Family Retreat Near Great Lakes Naval Base</a> <a href="/property/classic-workers-cottage-in-vibrant-bucktown-chicago/HA-3212893373" class="class="static-page-link"">Classic Workers Cottage in Vibrant Bucktown Chicago.</a> <a href="/property/stay-near-family-or-close-to-downtown-this-cottage-in-beverly-has-it-all/HA-3213848323" class="class="static-page-link"">Stay near family or close to downtown, this cottage in Beverly has it all!</a>

How much does it cost to rent a cottage in Chicago?

The average cost for a cottage rental in Chicago is $349 per night. Ownerdirect has a wide list of great cottages near Chicago that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Chicago that allow pets?

Yes, here are the top cottage rentals in Chicago that allow you to bring your pet: Riverfront Cottage Little Fox Cottage - A Cozy Riverview Getaway Fire Pit & Grill: Family Home on Fox River Trail! Cottingham Cottage <a href="/all/usa/illinois/chicago/178248" class="class="static-page-link"">See all pet-friendly vacation rentals in Chicago on Ownerdirect</a>

Do you have any rental cottages in Chicago that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chicago to find one that works for you.

Are there quality cottages in Chicago that have indoor swimming pools?

As of 2026, the data from Ownerdirect shows that there are Over 52 private swimming pools or cottages with indoor pools in the Chicago area along with other great amenities.