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/bella-villa-on-taylor-street-chicagos-little-italy-1-mile-west-the-loop-uic/HA-1217399612" class="class="static-page-link"">Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop &amp; UIC</a> <a href="/property/55th-floor-penthouse-with-award-winning-views/HA-3217757" class="class="static-page-link"">55th Floor Penthouse with Award-Winning Views</a> <a href="/property/3f-vintage-graystone-in-little-italy-near-loop-uic-united-ct-mccormick-place/HA-3212331854" class="class="static-page-link"">3F Vintage Graystone in Little Italy near loop UIC United Ct &amp; McCormick Place</a> <a href="/property/53-floor-magmile-penthouse-views-balcony-pool/HA-32172685" class="class="static-page-link"">53 Floor MagMile Penthouse Views, Balcony, Pool</a> <a href="/property/2-story-penthouse-views-fireplace-pool-gym/HA-321275170" class="class="static-page-link"">2-Story Penthouse Views, Fireplace, Pool, Gym</a> <a href="/property/new-luxury-penthouse-condo/HA-3212177560" class="class="static-page-link"">NEW LUXURY PENTHOUSE CONDO</a> <a href="/property/roscoe-village-inn-guesthouse-walk-to-chicago-s-wrigley-field/HA-321708795" class="class="static-page-link"">Roscoe Village Inn -Guesthouse - Walk to Chicago&#39;s Wrigley Field</a> <a href="/property/magic-factory-loft-2west/HA-321501599" class="class="static-page-link"">Magic Factory Loft 2West</a> <a href="/property/great-location-beautiful-friendly-andersonville-neighborhood/HA-321302224" class="class="static-page-link"">Great Location-Beautiful Friendly Andersonville Neighborhood</a> <a href="/property/single-family-home-sleeps-8-lincoln-park-lakeview/HA-321885106" class="class="static-page-link"">Single Family Home! Sleeps 8 Lincoln Park/Lakeview</a>

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

The average cost for a cottage rental in Chicago is $331 per night. Isleofpalmsresorts 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.

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 Isleofpalmsresorts shows that there are Over 11533 private swimming pools or cottages with indoor pools in the Chicago area along with other great amenities.

Chicago Cottage Rentals By Owner

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

From US $243

10.0 (239 Reviews)

Apartment

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

Air Conditioner
Parking
TV

Chicago Cottage Rentals & Holiday Homes

Find the best cottages in Chicago - We found 11533 exact matches

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