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/riverfront-cottage-sauna-nkayaks-dock-firepit/HA-3213984244" class="class="static-page-link"">Riverfront Cottage/sauna/nkayaks/dock/firepit</a> <a href="/property/4-the-cozy-cottage/HA-3213142920" class="class="static-page-link"">#4 The Cozy Cottage</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/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-coral-cottage/HA-3213142917" class="class="static-page-link"">The Coral Cottage</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/corporate-housing-for-travel-nurses-and-interns-located-near-o-hare-hospitals/HA-3213577748" class="class="static-page-link"">Corporate Housing for Travel Nurses and Interns Located Near O&#39;Hare &amp; Hospitals</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> <a href="/property/wanderlust-cottage/HA-3214095030" class="class="static-page-link"">Wanderlust Cottage</a> <a href="/property/lake-house-perfect-for-reunion/HA-3212578763" class="class="static-page-link"">Lake House Perfect for Reunion</a>

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

The average cost for a cottage rental in Chicago is $352 per night. Guidefororlando 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: Amazing summer lake escape in our waterfront cottage! Riverfront Cottage Classic Forest Park Foursquare Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports <a href="/all/usa/illinois/chicago/178248" class="class="static-page-link"">See all pet-friendly vacation rentals in Chicago on Guidefororlando</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 Guidefororlando shows that there are Over 51 private swimming pools or cottages with indoor pools in the Chicago area along with other great amenities.