
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 had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!

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.

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Now Open: Heated Pool with Entire House
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

Schaumburg Oasis:Private Pool & Enchanted Garden
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!

Stunning Home in Prime Chicago with Private Pool
Excellent place with lots to do. Local restaurants had delicious food, place was very clean and inviting. Will definitely be booking again in the future

Spacious 4 Bed/3.5 Bath Sleeps 8+
Beautiful house very clean and comfortable. We'll be back very soon

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

Cozy Home - Northwest side of Chicago
Great stay for a family trip! It was in a calm, quiet neighborhood where we felt safe that had all necessities! We did have a hard time with finding available parking on the street a few nights out of our visit, but other than that it was great and comfortable! We have already discussed visiting again and staying at Sarah’s!

Cheerful two bedroom home with patio/deck
Beautiful home in a quiet neighborhood with responsive and helpful hosts.

3BD/2BA Chicago Avondale/Logan Square House
Mia & Franco are great hosts going above and beyond to make our stay enjoyable, including leaving lovely roses to help celebrate our daughter's wedding weekend! We really enjoyed the back patio space and game tables. They were very responsive before, during and after our stay. We would definetly stay at Mia and Franco's again.

Garden/unit/1+1/cosy
First time staying at an Air Bnb and it was amazing. Instructions were very clear and the place had everything we needed!

Brand New Spacious Duplex
I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.

Vintage Urban Retreat | Oak Park
We had a great time at Gabriela's place. The listing was accurate, the location was great, and we were pleasantly surprised by how new and clean everything felt. Would stay again.

Family Home in Chicago-O'Hare
We love staying in this little house that’s actually quite big, wonderful outdoor area. Unfortunately it was too cold for us to enjoy it, but looked really amazing. Kitchen had everything we needed to enjoy our stay. Beds were extremely comfortable and hot water was fantastic. Close to the airport and convenient to lots of nice restaurants.

Spacious Family Haven
Such a great, family friendly place! We felt right at home and loved how it was stocked with everything we AND our kids would need! We also really enjoyed how conveniently located we were to a delicious coffee shop and grocer - huge perk when you're with kiddos! Would absolutely stay here again. :)
Private house rentals

Rooftop Access with Views and Gym - LCP Collection
Great place in a great location. Would definitely book again!

1mi to Beach | 2-Floor Loft | Foosball
The stay was amazing. The only issue was finding parking especially at night was really tuff to find a stop.

Alluring Avondale Abode
Our group had a great time in Beth’s place. Beth is very responsive and a great host. We will definitely use this space again in Chicago.

Luxe Limewash Getaway w/Sun Deck
We were a group of four teachers planning a girls get away. Elijah’s place was very nice. We asked if we could get in early and he sent us the code right away.He had put a case of water in the refrigerator which we really appreciated. The sectional in the living room was very comfortable and a great place for conversation. The patio in the back was great to sit outside. Overall, it was a very nice place to relax after busy days of sightseeing!

5BR's/3BA's/Large game room/fits13/Free prkng/3TVs
Great stay for a 3-night family getaway. Appreciated the bunk-bed room for kids. (With toys!) The game room in the basement was a hit, but watch your head if you are tall. Overall great value for a large group (we had 10), especially with kids, but the construction on I-90 (obviously not the fault of the owner) makes getting to and from downtown a major chore.

Charming Oak Park 4bd/3.5ba and 2 Private Parking
David’s place was AWESOME!! Everything was great and homie. David was awesome with responding and made sure we were good. I had two past reviews in which they could have easily sparked David to not let me book with him. But he was open minded and heard me out unlike some other host. All reviews are not honest and the details can be off by mishaps. But I appreciate his openness, niceness and overall just awesomeness. Definitely an awesome place for an affordable price. The neighborhood is nice as well and a great out door seating area in the back yard. I’ll be booking again. THANK YOU DAVID ❤️

Cozy getaway in the city.
Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.

Game Room • Fire-pit • Playground • Gym • Billiard
Bre and Peter were fantastic hosts and their home is beautiful. As hosts they were extremely responsive and their home was amazing. I would HIGHLY recommend them and if I ever visit Chicago again I know where I’ll be staying. ⭐️⭐️⭐️⭐️⭐️
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club