
House holiday rentals in Cook County
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Top-rated house rentals in Cook County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Cook County
House rentals with a pool

Home
4.93 out of 5 average rating, 44 reviewsCozy house in Schererville
kates house was excellent and clean extremely comfortable for a work trip.

Home
5 out of 5 average rating, 10 reviewsMunster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Home
4.95 out of 5 average rating, 43 reviewsWhole House with a Hot Tub!
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.

Home
4.83 out of 5 average rating, 35 reviewsEntire House With Pool - Backyard Beach Getaway
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

Home
4.87 out of 5 average rating, 15 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Marzena’s place was great…again. This is my second time renting from her. The place is spotless and she is awesome with her response time. So easy to deal with. I highly recommend and will stay there again Thanks Marzena!!!

Home
4.87 out of 5 average rating, 53 reviewsLuxury Cabin in Lakeview
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!

Home
4.93 out of 5 average rating, 75 reviewsBeautiful Spanish style Home (w/inground pool)
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.

Home
4.8 out of 5 average rating, 55 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
It was a wonderful experience staying at evolves home. It was very clean, and spacious enough for all my siblings to be comfortable.
Weekly house rentals

Home
4.94 out of 5 average rating, 33 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!

Home
4.92 out of 5 average rating, 271 reviewsDuplex Home RoscoeVillage/Wrigley Free St Parking
Sharlene was an excellent host. She gave us suggestions on what we could do in the area and was very responsive. Her home looked just like the pictures and was very clean. We had a hiccup at checkout and she was very accommodating. We would definitely book her home again.

Home
4.81 out of 5 average rating, 58 reviewsIndiana Dunes Park Getaway w/Firepit, Near Beach
Kelly’s place was wonderful. There’s a lot to enjoy here from a wonderful backyard with a fire pit, a lovely front porch, a chill side porch with a grill, a second floor balcony, and a sun room. The place was perfectly clean when I got there and they so nicely left out plenty of clean towels and sweatshirts for myself and my friends. I would definitely stay again if I came back to the area!

Home
4.97 out of 5 average rating, 31 reviewsWicker Park 6bd/4ba, Steps from Cta, Parking Incl
Tom was great, friendly, and very helpful, highly recommend

Home
4.98 out of 5 average rating, 47 reviewsSuburban Serenity~Grill, Fire pit, Big yard~
Great stay..nice, cozy home. Above and beyond well-maintained and very clean.

Home
4.84 out of 5 average rating, 146 reviewsThe Spa of Downtown Whiting
Wonderful stay for our short trip, next level clean and fantastic

Home
4.95 out of 5 average rating, 182 reviewsWrigleyville Greystone
The place was in a beautiful, quiet neighborhood, and clean and very comfortable for our family of 5 adults. Mark was very accommodating and let us check in two hours early as we arrived in town before we expected to, and it was raining and didn't want to get wet walking around outside. The location was great as we were in town for the NHL Winter Classic, and it was an easy walk to Wrigley Field. Also, lots of great restaurants within walking distance. We were also celebrating Christmas with our family and to our wonderful surprise, there was a tree and many other festive decorations up that made it extra special! We would definitely stay in this location again while in Chicago.

Home
4.94 out of 5 average rating, 220 reviews3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin
It was a great place to have family dinners with a big dining room table. The kitchen was great. The bedrooms were great. Definitely recommend staying here.
Private house rentals

Home
5 out of 5 average rating, 4 reviewsSleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.

Home
4.94 out of 5 average rating, 16 reviewsWarm bungalow in New City
Nice house 🔥

Home
4.95 out of 5 average rating, 39 reviewsGorgeous and Luxurious 3 BR Home
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.

Home
4.88 out of 5 average rating, 48 reviewsGrand Victorian Mansion in Austin Area
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.

Home
4.81 out of 5 average rating, 188 reviewsWarm and comfortable inviting Suburban home !
Rich was great. I appreciated his advice on getting around the area and he was quick to respond on checkout - really enjoyed my stay

Home
4.88 out of 5 average rating, 32 reviewsThe Blue House: Family Retreat
Very homey place and they even decorated for Valentine’s Day I loved it!! Will be booking again!

Home
4.8 out of 5 average rating, 5 reviewsRelax & Rejuvenate
AMAZING LOCATION! I'd like to point out that I stayed in this location for a month. I'd also like to point out that I will be returning. This place was very clean, neat and newly renovated. I have a phobia of bugs and didn't encounter anything the entire stay. The neighbors were very nice. The block was peaceful and not to busy. Not to mention Nikki was the best host that I could've ever asked for. She was extremely responsive and very personable.

Home
4.93 out of 5 average rating, 113 reviewsQuiet cul-de-sac with huge fenced in backyard
Great stay felt safe and peaceful will stay again had everything we needed for our trip Tom was outstanding host bonfire was amazing water was hot love everything about the place thanks Tom
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