
House vacation rentals in Northwest Side
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Top-rated house rentals in Northwest Side
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Vacation rentals for every style
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Popular amenities for Northwest Side house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

Munster 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.

No Cleaning Fee - Whole House With Hot Tub
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.

Schaumburg Oasis with a Pool and Hidden Garden
Was in town for a weekend and the place was a great fit for our group of 4 people! I really wish we got to go during the warmer weather to enjoy the huge back yard. Would definitely recommend staying at Marzena's place. Everything was clean, organized, and really nice decorations that themed each room. It was just the right amount too; definitely felt like the walls weren't bare, but not too busy. The whole experience made it seem like we were staying at a friend's home an not a stranger's house.

Luxury Cabin in Lakeview
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!

Large 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.

Beautiful 137 Year Old Farm Home (3night min)
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

Spacious 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

Duplex Home RoscoeVillage/Wrigley Free St Parking
Sharleen is such a nice person and host. Her place is really accommodating and comfortable, our team had a great time at her home. Thank you, Sharleen.

Cozy at the Walter
Our go to in the Chicagoland area.... always a pleasure to stay at The Walter

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
Tom was great, friendly, and very helpful, highly recommend

The Avondale Guesthouse
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!

The Spa of Downtown Whiting
Really enjoyed Steven’s place! It was comfortable and spacious, and had everything we needed. Great location that’s not far from Chicago, and lots of shops and restaurants just blocks away. Cute little neighborhood and small town feel. Steven was easy to work with and really responsive. Would love to stay again when we’re in the area!

Wrigleyville 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.

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin
Great place with plenty of space. Our family really enjoyed Michael’s home.

RANCH, House-tel: updated full kitchen, comfy beds
What a great Airbnb! Easy to access downtown Chicago but without the hassle of being downtown. Everything was super clean, the beds are comfortable and the neighborhood is quiet and easy to walk (especially if you have pets). Highly recommend!
Private house rentals

Spacious family friendly home away from home
This was perfect for our needs for 6 people. There was plenty of space for sleeping and just hanging out without feeling crowded. It was clean and very neat. It was also nice to have a Roku TV so we could stream our apps. We had a great visit.

Sleeps 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.

Warm bungalow in New City
Nice house 🔥

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd
Perfect for our work trip!

Grand 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.

Warm and comfortable inviting Suburban home !
Great host, nice peaceful home with old-fashioned feel. We even met some friendly neighbors. Rich always responded promptly to questions & was overall kind & accommodating. We enjoyed the area, including many historical homes, local restaurants (DeMar’s😋) and a beautiful event at the iconic Lyric Theater. Thank you!

The Blue House: Family Retreat
Very Good place

Quiet cul-de-sac with huge fenced in backyard
Most amazing place to stay 5/5 would recommend.
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