House holiday rentals in Oak Park
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Top-rated house rentals in Oak Park
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 house rentals in Oak Park
House rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
24–31 Aug
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
23–30 Jul
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
7–14 Jul
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
12–19 Nov
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
2–9 Feb
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
7–14 Aug
Home in Bartlett
5.0 out of 5 average rating, 4 reviewsFully Furnished Executive Home, Lux Amenities
11–18 Dec
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
29 Jul – 5 Aug
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
29 Jun – 6 Jul
Home in Oak Park
4.95 out of 5 average rating, 37 reviewsCozy & comfy w/free parking & W/D
14–19 Jul
Home in Oak Park
5.0 out of 5 average rating, 4 reviewsBright Studio Newly Remodeled
1–8 Jul
Home in Forest Park
4.94 out of 5 average rating, 67 reviewsAdorable house Madison Street w/ 2 car garage!
10–17 Nov
Home in Oak Park
4.8 out of 5 average rating, 15 reviewsThe Maple Place
24 Jun – 1 Jul
Home in Berwyn
5.0 out of 5 average rating, 77 reviewsRetro Modern Bungalow | free parking | fire pit
15–22 Nov
Home in Maywood
4.83 out of 5 average rating, 60 reviewsMaywood Relaxation
21–28 Feb
Home in Oak Park
4.97 out of 5 average rating, 59 reviewsModern Victorian Charm | A+ Location in OP
18–25 Sept
Private house rentals
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
19–26 Jan
Home in Forest Park
4.88 out of 5 average rating, 65 reviews5 Bedroom - Next to Restaurants and Shopping
11–18 Dec
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
11–18 Sept
Home in Oak Park
5.0 out of 5 average rating, 15 reviewsOak Park 3000 sq ft, sleeps 16
8–15 Aug
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
30 Nov – 7 Dec
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
4–11 Dec
Home in Berwyn
4.95 out of 5 average rating, 22 reviewsBerwyn Beauty
16–23 Feb
Home in Oak Park
5.0 out of 5 average rating, 21 reviewsThe Oak Park Game Room 15 mins to Chicago Loop
1–8 Jul
Quick stats about house rentals in Oak Park
Total rentals
130 properties
Wifi availability
120 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2.9K reviews
Destinations to explore
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