House vacation rentals in Northwest Side

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Popular amenities for Northwest Side house rentals

House rentals with a pool

Guest favorite
Home in Highland Park
4.91 out of 5 average rating, 145 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

MaryRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars5 months 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.
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars4 weeks ago
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!
Guest favorite
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
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.
Guest favorite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars1 day ago
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!
Home in Chicago
4.63 out of 5 average rating, 8 reviews

Stunning Home in Prime Chicago with Private Pool

BrianRating, 5 stars1 month ago
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
Guest favorite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars8 months ago
Beautiful house very clean and comfortable. We'll be back very soon
Guest favorite
Home in Schaumburg
4.95 out of 5 average rating, 22 reviews

Paradise 4BR w/ Pool & Games

MariaRating, 5 stars1 month ago
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

Superhost
Home in Chicago
4.76 out of 5 average rating, 49 reviews

Cozy Home - Northwest side of Chicago

KyannaRating, 5 stars1 day ago
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!
Top guest favorite
Home in Chicago
4.97 out of 5 average rating, 32 reviews

Cheerful two bedroom home with patio/deck

EricRating, 5 stars3 months ago
Beautiful home in a quiet neighborhood with responsive and helpful hosts.
Guest favorite
Home in Chicago
4.9 out of 5 average rating, 62 reviews

3BD/2BA Chicago Avondale/Logan Square House

JillRating, 5 starstoday
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.
Superhost
Home in Chicago
4.74 out of 5 average rating, 23 reviews

Garden/unit/1+1/cosy

GabriellaRating, 5 stars2 weeks ago
First time staying at an Air Bnb and it was amazing. Instructions were very clear and the place had everything we needed!
Superhost
Home in Chicago
4.83 out of 5 average rating, 71 reviews

Brand New Spacious Duplex

LillianRating, 5 stars1 week ago
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.
Top guest favorite
Home in Oak Park
4.94 out of 5 average rating, 34 reviews

Vintage Urban Retreat | Oak Park

BrianRating, 5 stars1 day ago
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.
Guest favorite
Home in Chicago
5 out of 5 average rating, 37 reviews

Family Home in Chicago-O'Hare

KathyRating, 5 stars2 months ago
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.
Guest favorite
Home in Chicago
5 out of 5 average rating, 10 reviews

Spacious Family Haven

MalloryRating, 5 stars3 months ago
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

Superhost
Home in Oak Park
4.78 out of 5 average rating, 87 reviews

Rooftop Access with Views and Gym - LCP Collection

CynthiaRating, 5 stars1 week ago
Great place in a great location. Would definitely book again!
Guest favorite
Home in Chicago
4.93 out of 5 average rating, 28 reviews

1mi to Beach | 2-Floor Loft | Foosball

MarcelloRating, 5 stars2 weeks ago
The stay was amazing. The only issue was finding parking especially at night was really tuff to find a stop.
Top guest favorite
Home in Chicago
5 out of 5 average rating, 17 reviews

Alluring Avondale Abode

AliceRating, 5 stars1 week ago
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.
Guest favorite
Home in Skokie
4.97 out of 5 average rating, 76 reviews

Luxe Limewash Getaway w/Sun Deck

LindaRating, 5 stars1 week ago
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!
Guest favorite
Home in Chicago
5 out of 5 average rating, 25 reviews

5BR's/3BA's/Large game room/fits13/Free prkng/3TVs

ChaseRating, 5 stars2 weeks ago
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.
Guest favorite
Home in Oak Park
4.86 out of 5 average rating, 36 reviews

Charming Oak Park 4bd/3.5ba and 2 Private Parking

MelvinaRating, 5 stars2 weeks ago
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 ❤️
Guest favorite
Home in Burbank
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars1 week ago
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.
Guest favorite
Home in Chicago
4.97 out of 5 average rating, 36 reviews

Game Room • Fire-pit • Playground • Gym • Billiard

BrentRating, 5 stars1 week ago
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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