House accommodation & holiday rentals in Chicago
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Top-rated house accommodation & rentals in Chicago
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago house rentals
House rentals with a pool
Home in Highland Park
4.91 out of 5 average rating, 128 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Chicago
4.82 out of 5 average rating, 17 reviews2Bed+2Bath PentHouse in South Loop
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Weekly house rentals
Home in Chicago
4.95 out of 5 average rating, 133 reviewsChicago Riverhouse summer on our patio!
Home in Chicago
4.89 out of 5 average rating, 377 reviewsPro Cleaned & Isolated West Loop Coach House
Home in Bolingbrook
4.92 out of 5 average rating, 103 reviewsThe Sunshine Spot
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Home in Chicago
4.92 out of 5 average rating, 113 reviewsSpacious Two Story Luxurious Home w/Outdoor Deck!
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.91 out of 5 average rating, 92 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
4.9 out of 5 average rating, 30 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Private house rentals
Home in Chicago
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Home in Chicago
4.85 out of 5 average rating, 84 reviewsFree parking, close to public transit, dining
Home in Chicago
4.97 out of 5 average rating, 72 reviewsEntire first floor in Lincoln Square!
Home in Palatine
4.86 out of 5 average rating, 42 reviewsPrivate Room with attach bath and personal kitchen
Home in Chicago
4.98 out of 5 average rating, 52 reviewsCity Cottage in Logan Square-Avondale
Home in Munster
5.0 out of 5 average rating, 18 reviewsCozy Farmhouse in Munster
Home in Chicago
5.0 out of 5 average rating, 19 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
4.98 out of 5 average rating, 88 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Quick stats about house rentals in Chicago
Total rentals
1.8K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
950 properties are a good fit for families
Total number of reviews
69K reviews
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