House holiday rentals in Northwest Side

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Popular amenities for Northwest Side house rentals

House rentals with a pool

Guest favourite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

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

JeffRating, 5 stars3 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.
Guest favourite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars2 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 favourite
Home in Bloomingdale
4.93 out of 5 average rating, 44 reviews

No Cleaning Fee - Whole House With Hot Tub

ChristopherRating, 5 stars1 month ago
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.
Guest favourite
Home in Schaumburg
4.89 out of 5 average rating, 18 reviews

Schaumburg Oasis with a Pool and Hidden Garden

NickRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Chicago
4.87 out of 5 average rating, 53 reviews

Luxury Cabin in Lakeview

Varun Rating, 5 stars6 months ago
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!
Guest favourite
Home in Plainfield
4.93 out of 5 average rating, 75 reviews

Large Spanish style Home (w/inground pool)

DevonRating, 5 stars5 months ago
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.
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars7 months ago
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!
Home in Glenwood
4.8 out of 5 average rating, 55 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

JosiahRating, 5 stars3 months ago
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

Guest favourite
Home in Chicago
4.92 out of 5 average rating, 273 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

marcioRating, 5 stars1 week ago
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.
Guest favourite
Home in Lansing
4.82 out of 5 average rating, 116 reviews

Cozy at the Walter

TehaniRating, 5 stars3 weeks ago
Our go to in the Chicagoland area.... always a pleasure to stay at The Walter
Top Guest favourite
Home in Chicago
4.97 out of 5 average rating, 31 reviews

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

SpencerRating, 5 stars2 months ago
Tom was great, friendly, and very helpful, highly recommend
Guest favourite
Home in Chicago
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars5 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!
Superhost
Home in Whiting
4.84 out of 5 average rating, 147 reviews

The Spa of Downtown Whiting

JaniceRating, 5 stars3 weeks ago
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!
Top Guest favourite
Home in Chicago
4.95 out of 5 average rating, 182 reviews

Wrigleyville Greystone

MarkRating, 5 stars2 months ago
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.
Guest favourite
Home in Justice
4.94 out of 5 average rating, 223 reviews

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

PaulRating, 5 stars3 weeks ago
Great place with plenty of space. Our family really enjoyed Michael’s home.
Top Guest favourite
Home in Itasca
5 out of 5 average rating, 49 reviews

RANCH, House-tel: updated full kitchen, comfy beds

DianaRating, 5 stars3 months ago
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

Guest favourite
Home in Aurora
4.94 out of 5 average rating, 36 reviews

Spacious family friendly home away from home

BrendaRating, 5 stars2 months ago
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.
Superhost
Home in Oak Park
5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars2 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.
Superhost
Home in Chicago
4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

ErnestoRating, 5 stars6 months ago
Nice house 🔥
Guest favourite
Home in Schaumburg
4.96 out of 5 average rating, 54 reviews

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd

KinseyRating, 5 stars3 days ago
Perfect for our work trip!
Superhost
Home in Chicago
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars4 months ago
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.
Superhost
Home in Blue Island
4.81 out of 5 average rating, 190 reviews

Warm and comfortable inviting Suburban home !

LuCindaRating, 5 stars3 weeks ago
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!
Superhost
Home in Gary
4.89 out of 5 average rating, 37 reviews

The Blue House: Family Retreat

ChristianRating, 5 stars1 day ago
Very Good place
Top Guest favourite
Home in Chicago Ridge
4.93 out of 5 average rating, 116 reviews

Quiet cul-de-sac with huge fenced in backyard

LatrinaRating, 5 stars2 weeks ago
Most amazing place to stay 5/5 would recommend.

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