House holiday rentals in Cook County

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Popular amenities for house rentals in Cook County

House rentals with a pool

Guest favourite

Home

4.93 out of 5 average rating, 44 reviews

Cozy house in Schererville

DanielRating, 5 stars1 week ago
kates house was excellent and clean extremely comfortable for a work trip.
Guest favourite

Home

5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars1 month ago
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.
Guest favourite

Home

4.95 out of 5 average rating, 43 reviews

Whole House with a Hot Tub!

ChristopherRating, 5 stars2 weeks ago
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.
Superhost

Home

4.83 out of 5 average rating, 35 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars2 months ago
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
Guest favourite

Home

4.87 out of 5 average rating, 15 reviews

Schaumburg Oasis with a Pool and Hidden Garden

LisaRating, 5 stars1 month ago
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!!!
Guest favourite

Home

4.87 out of 5 average rating, 53 reviews

Luxury Cabin in Lakeview

Varun Rating, 5 stars5 months ago
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!
Guest favourite

Home

4.93 out of 5 average rating, 75 reviews

Beautiful Spanish style Home (w/inground pool)

DevonRating, 5 stars4 months ago
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 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

JosiahRating, 5 stars2 months ago
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

Guest favourite

Home

4.94 out of 5 average rating, 33 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

NoelleRating, 5 stars1 week ago
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!
Guest favourite

Home

4.92 out of 5 average rating, 271 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

JaleesaRating, 5 stars3 weeks ago
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.
Superhost

Home

4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars5 months ago
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!
Guest favourite

Home

4.97 out of 5 average rating, 31 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

SpencerRating, 5 stars2 months ago
Tom was great, friendly, and very helpful, highly recommend
Guest favourite

Home

4.98 out of 5 average rating, 47 reviews

Suburban Serenity~Grill, Fire pit, Big yard~

MAHGULLRating, 5 stars2 weeks ago
Great stay..nice, cozy home. Above and beyond well-maintained and very clean.
Superhost

Home

4.84 out of 5 average rating, 146 reviews

The Spa of Downtown Whiting

BradleyRating, 5 stars1 month ago
Wonderful stay for our short trip, next level clean and fantastic
Guest favourite

Home

4.95 out of 5 average rating, 182 reviews

Wrigleyville Greystone

MarkRating, 5 stars1 month ago
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.
Guest favourite

Home

4.94 out of 5 average rating, 220 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

DanaRating, 5 stars3 months ago
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

Superhost

Home

5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars1 month ago
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.
Guest favourite

Home

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

ErnestoRating, 5 stars5 months ago
Nice house 🔥
Guest favourite

Home

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars3 months ago
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.
Superhost

Home

4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars3 months ago
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.
Superhost

Home

4.81 out of 5 average rating, 188 reviews

Warm and comfortable inviting Suburban home !

MikeRating, 5 stars1 week ago
Rich was great. I appreciated his advice on getting around the area and he was quick to respond on checkout - really enjoyed my stay
Superhost

Home

4.88 out of 5 average rating, 32 reviews

The Blue House: Family Retreat

KasiyahRating, 5 stars1 day ago
Very homey place and they even decorated for Valentine’s Day I loved it!! Will be booking again!
Superhost

Home

4.8 out of 5 average rating, 5 reviews

Relax & Rejuvenate

LolaRating, 5 stars13 months ago
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.
Guest favourite

Home

4.93 out of 5 average rating, 113 reviews

Quiet cul-de-sac with huge fenced in backyard

JermiahRating, 5 stars1 week ago
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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