Cottage vacation rentals in Chicago
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Top-rated cottage rentals in Chicago
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago cottage rentals
Cottage rentals with free parking
Room in West Chicago
Klara's Cottage
Jun 14 – 21
Room in North Riverside
4.92 out of 5 average rating, 172 reviewsThe Albany Park Room at the Cape Cod in Riverside
Aug 27 – Sep 3
Cottage in Merrillville
4.89 out of 5 average rating, 185 reviewsThe Hideaway
Sep 30 – Oct 7
Cottage in Gary
4.82 out of 5 average rating, 11 reviewsCozy Home near Chicago, Casinos, Shops, & Parks
Nov 1 – 8
Cottage in Fox River Grove
4.94 out of 5 average rating, 52 reviewsLittle Fox Cottage - A Cozy Riverview Getaway
Sep 4 – 11
Cottage in Highland Park
4.96 out of 5 average rating, 48 reviewsRe-imagined 1880s cottage by Highwood, Metra, Lake
Oct 23 – 30
Cottage in Gary
4.94 out of 5 average rating, 32 reviewsMiller Beach Cozy Cottage with indoor fireplace
Mar 30 – Apr 6
Cottage in Barrington
5.0 out of 5 average rating, 61 reviewsCozy French Inspired Cottage in rural setting
Jan 30 – Feb 6
Pet-friendly cottage rentals
Cottage in Gary
4.88 out of 5 average rating, 60 reviewsLuxury Cottage nestled in nature, close to beach
Aug 29 – Sep 5
Cottage in Gary
5.0 out of 5 average rating, 7 reviewsMiller Beach Cottage
May 7 – 14
Cottage in Gary
4.82 out of 5 average rating, 11 reviewsCozy Home near Chicago, Casinos, Shops, & Parks
Nov 1 – 8
Cottage in Gary
4.7 out of 5 average rating, 93 reviewsHome Theatre +Fire Pit+Enclosed Porch +
Jan 17 – 24
Cottage in Naperville
New place to stayHome: Your Cozy Getaway
Jul 13 – 18
Cottage in Gary
3.92 out of 5 average rating, 12 reviewsCozy beach cottage w/ hot tub near West Beach.
Sep 9 – 16
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with a balcony Chicago
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- Monthly Rentals Chicago
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