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
4.92 out of 5 average rating, 142 reviews

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

JeffRating, 5 stars5 months ago
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.
Home in Glen Ellyn
4.8 out of 5 average rating, 5 reviews

Pardizes Suites

FernandaRating, 5 stars1 week ago
Really nice and spacious place. Everything was clean and comfy.
Guest favorite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars4 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.
Top guest favorite
Home in Bloomingdale
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars2 weeks ago
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
Guest favorite
Home in Schaumburg
4.91 out of 5 average rating, 22 reviews

Schaumburg Oasis with a Pool and Hidden Garden

GotimukulRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Plainfield
4.93 out of 5 average rating, 76 reviews

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars6 days ago
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!!
Home in Glenwood
4.8 out of 5 average rating, 56 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

Nicole And ArnoRating, 5 stars1 month ago
Loved this Airbnb! Didn’t want to leave.
Guest favorite
Home in Schaumburg
4.95 out of 5 average rating, 21 reviews

Paradise 4BR w/ Pool & Games

MariaRating, 5 stars3 days 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

Guest favorite
Home in Chicago
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars6 days ago
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. 🙂
Guest favorite
Home in Chicago
4.98 out of 5 average rating, 152 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Kevin And CourtneyRating, 5 stars2 months ago
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.
Guest favorite
Home in Lansing
4.82 out of 5 average rating, 117 reviews

Cozy at The Walter

JodimarieRating, 5 stars3 weeks ago
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!!
Top guest favorite
Home in Chicago
4.97 out of 5 average rating, 33 reviews

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

LaureenRating, 5 stars1 month ago
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.
Guest favorite
Home in Chicago
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars6 months ago
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!
Guest favorite
Home in Whiting
4.84 out of 5 average rating, 153 reviews

The Spa of Downtown Whiting

YesyRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Chicago
4.95 out of 5 average rating, 184 reviews

Wrigleyville Greystone

ThomasRating, 5 stars1 month ago
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!
Guest favorite
Home in Justice
4.93 out of 5 average rating, 224 reviews

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

PaulRating, 5 stars2 months ago
Great place with plenty of space. Our family really enjoyed Michael’s home.

Private house rentals

Guest favorite
Home in Aurora
4.92 out of 5 average rating, 39 reviews

Spacious family friendly home away from home

KatieRating, 5 stars1 week ago
This was a great stay, I definitely would come here again!! The host was very responsive and friendly!! I enjoyed the area very much!!😀
Top guest favorite
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars4 months 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.
Top guest favorite
Home in Elmhurst
5 out of 5 average rating, 48 reviews

Big Family Home with 4 King Beds

GabrielRating, 5 stars6 days ago
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
Superhost
Home in Blue Island
4.82 out of 5 average rating, 195 reviews

Warm and comfortable inviting Suburban home !

CasieRating, 5 stars6 days ago
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.
Superhost
Home in Gary
4.87 out of 5 average rating, 45 reviews

The Blue House: Family Retreat

AlexisRating, 5 stars2 weeks ago
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!!
Superhost
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
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.
Top guest favorite
Home in Chicago Ridge
4.92 out of 5 average rating, 126 reviews

Quiet cul-de-sac with huge fenced in backyard

CandaceRating, 5 stars1 week ago
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!
Superhost
Home in Homer Glen
5 out of 5 average rating, 3 reviews

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars71 months ago
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.

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