Lake house holiday rentals in Chicago
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Top-rated lakehouse rentals in Chicago
Guests agree: These lakehouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chicago lakehouse rentals
Waterfront lakehouse rentals
Home in Chicago
5.0 out of 5 average rating, 52 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
12–19 Aug
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
10–17 Oct
Home in Barrington
5.0 out of 5 average rating, 25 reviewsON RIVER Barrington Home + Deck & Views
31 Jan – 7 Feb
Home in Westmont
4.89 out of 5 average rating, 18 reviewsCozy 5-bedroom with lake views and spacious deck
4–11 Jan
Home in Chicago
4.82 out of 5 average rating, 60 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
2–9 Nov
Home in Des Plaines
4.25 out of 5 average rating, 4 reviewsHouse 1 minute from O'hare Airport
12–19 Jan
Home in Fox River Grove
Riverfront, Walk to the Norge Ski Jump & Metra!
20–27 Jul
Room in Chicago
4.83 out of 5 average rating, 103 reviewsRenovated space in a historic row house.
5–12 Nov
Pet-friendly lake house rentals
Home in Highland Park
4.86 out of 5 average rating, 43 reviewsA Wonderful Getaway Home on the North Shore!
6–13 Dec
Home in Lombard
4.69 out of 5 average rating, 35 reviewsBlue Heron Lodge
6–13 Jul
Home in Westmont
4.95 out of 5 average rating, 22 reviewsWestmont,Il 4/3 on the Lake
17–24 Jan
Home in Bolingbrook
4.81 out of 5 average rating, 21 reviewsPeaceful Bolingbrook Getaway
10–17 Feb
Home in Des Plaines
4.5 out of 5 average rating, 123 reviewsEntire House Minutes from O’Hare Airport!! By lake
25 Jan – 1 Feb
Room in Des Plaines
4.89 out of 5 average rating, 314 reviewsR2 Cozy room in a convenient location by a river
26 May – 2 Jun
Room in Evanston
5.0 out of 5 average rating, 10 reviewsLuxury Master Suite w/Jacuzzi
15–22 Mar
Room in Lake Barrington
4.89 out of 5 average rating, 27 reviewsSuperior Splendor on Shoreline
2–9 Oct
Private lake house rentals
Home in Chicago
4.88 out of 5 average rating, 24 reviewsClean 5 Star 2 BR Greystone, Heart of Logan Square
18–25 Nov
Home in Chicago
5.0 out of 5 average rating, 26 reviews3 floor, 2000 sq ft home - central & clean!
20–27 Oct
Home in Chicago
4.89 out of 5 average rating, 45 reviewsHistoric Hyde Park 4 bedroom house
18–25 Mar
Home in Chicago
4.82 out of 5 average rating, 96 reviewsWoodlawn Oasis: 5-15 Mins from Food, Fun, Dining
13–20 Nov
Home in Streamwood
4.85 out of 5 average rating, 13 reviewsCozy Retreat in a Prime location
21–28 Sep
Home in Chicago
4.86 out of 5 average rating, 21 reviewsExec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
11–18 Aug
Home in Chicago
4.6 out of 5 average rating, 5 reviewsEly's Landing~Condo Near 71st Beach,Golf & Museums
18–25 Feb
Home in Evanston
5.0 out of 5 average rating, 11 reviewsStunning Coach House in Evanston, near Lake/NU
2–9 Aug
Destinations to explore
- Downtown Chicago Holiday rentals
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