
House vacation rentals in Northwest Side
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Top-rated house rentals in Northwest Side
Guests agree: these houses are highly rated for location, cleanliness, and more.
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.

Pardizes Suites
Really nice and spacious place. Everything was clean and comfy.

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.

Whole House With Hot Tub And Spacious Bedrooms
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

Schaumburg Oasis with a Pool and Hidden Garden
had such a wonderful stay! The place was exactly as described—clean, cozy, and beautifully maintained. The host was incredibly kind and responsive, making the whole experience smooth and stress-free. Would definitely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!

Beautiful Spanish style Home (w/inground pool)
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

Spacious Family Glenwood Estates Home w/ Hot Tub!
Loved this Airbnb! Didn’t want to leave.

Paradise 4BR w/ Pool & Games
We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.
Weekly house rentals

Duplex Home RoscoeVillage/Wrigley Free St Parking
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂

Spacious Five Bedroom Home in Trendy Chicago Neighborhood
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.

Cozy at The Walter
Lovely cozy home perfect for what we needed. Loved the yummy extras she left for us in the kitchen:) The beds were comfortable and there were plenty of extra comforters for the cold nights! The heater worked amazingly well and the home smelled so nice of mild sandalwood from a diffuser in the living room. We felt right at home, and the location for us worked out well! Thank you!!

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.

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
Thank you for allowing us to enjoy your home. It was a wonderful experience. It is incredible. The place is very cozy. You feel an atmosphere of relaxation and peace.

Wrigleyville Greystone
Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!

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

Spacious family friendly home away from home
This was a great stay, I definitely would come here again!! The host was very responsive and friendly!! I enjoyed the area very much!!😀

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.

Big Family Home with 4 King Beds
I will be recommending this place to everyone for a nice get together. The neighborhood was nice and quiet and it is a beautiful place to relax or to have as an activity weekend. Plenty of stuff to do

Warm and comfortable inviting Suburban home !
Nice spot - place was very clean, comfy beds, lots of seating areas that were also comfy. We got used the the sounds of the trains after the first night. Bumped into Rich one day while he was mowing the grass; he was very kind. The place is a little older, but that’s in the description. We couldn’t figure out how to get the stove to turn on so we heated food in the microwave and on the gas grill outside. Neighborhood was very quiet and peaceful, and we liked having the fenced yard for our dog.

The Blue House: Family Retreat
Clean and kid friendly! Just as described. Perfect place to hang our Easter vacation with our group of 13!! Everyone felt comfortable and accommodated. Only thing I’d change if I could, more pillows! We’re a pillow loving family. Otherwise everything was great!!

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Quiet cul-de-sac with huge fenced in backyard
Tom’s place felt right at home! Spacious backyard, quiet neighborhood, and he’s very friendly. Responded right away with any questions or comments we had! 10/10 recommend anyone to stay here if available!

4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- Wilmot Mountain Ski Resort
- The Field Museum
- Wicker Park
- Lincoln Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Brookfield Zoo
- Flossmoor Golf Club
- Illinois Beach State Park
- Garfield Park Conservatory
- Skokie Country Club
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