House vacation rentals in North Side

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Popular amenities for North Side house rentals

House rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.
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
A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars5 months ago
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.
A well-lit living area features warm wood flooring and neutral walls. A decorative chair with a floral pattern adds a splash of color. A small television is mounted on the wall, complemented by a simple black media stand, allowing for relaxed entertainment.
Home in Schaumburg
4.78 out of 5 average rating, 9 reviews

Spacious 3 Floor Townhome

AndresRating, 5 stars2 days ago
My spouse and I couldn't of had a better weekend without Alex's listing! Everything was as Alex had described it in the post. It was close to restaurants, grocery stores and entertainment needs. Alex made it easy check in and check out. We would definitely recommend this place to any couple or small family.
Top guest favorite
A clear swimming pool is surrounded by lush greenery and a wooden deck. Lounge chairs are placed nearby, and a colorful inflatable pool float rests on the water's surface. Sunlight reflects off the pool, enhancing its inviting blue color.
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
An inviting above-ground pool is surrounded by a wooden deck, featuring a secure entry gate. The pool is set in a spacious backyard, with green grass and trees providing a natural backdrop. The clear blue water glistens under the daylight.
Home in Schaumburg
4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars8 months ago
We really enjoyed our stay at this beautiful home. It is close to everything. The place is clean and very organized. Lily and Nathan has been wonderful and very responsive and communicated well with us. I definitely recommend this place when you visit Schaumburg. Thank you guys for everything.
Guest favorite
An inviting backyard scene features a sparkling in-ground pool surrounded by lounge chairs and shaded by greenery. The house's exterior showcases large glass doors that open onto the patio area, providing a seamless connection between indoor and outdoor spaces.
Home in Schaumburg
4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

LindsayRating, 5 stars3 months ago
Everything went perfect for us. We flew in from out of town, and some plans fell through. We asked Mike if it was possible to check in a couple hours early and he was very flexible. We really appreciate you and your home. Thanks for letting us stay.

Weekly house rentals

Guest favorite
A well-lit entryway showcases a wooden staircase with elegant railing leading to upper levels. The dark front door contrasts with the light walls, while a stylish cabinet and framed photos add character to the space, inviting guests into the home.
Home in Chicago
4.92 out of 5 average rating, 281 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars2 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
A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.
Home in Glen Ellyn
4.92 out of 5 average rating, 148 reviews

Home in Glen Ellyn

LindaRating, 5 stars2 days ago
Humongous place to stay for a large group. Master bedroom was so huge! Having 5 bedrooms was great. We really enjoyed our stay.
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.
Top guest favorite
A bright dining area features a long wooden table surrounded by six blue chairs. A modern chandelier hangs above, illuminating the space. In the background, a staircase leads to the upper level, while a cozy living area is visible, providing an open and inviting layout.
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
A comfortable living room is visible, featuring two sofa sets arranged around a coffee table on a soft area rug. A flat-screen TV is mounted on the wall, with a ceiling fan above providing a sense of airflow. Natural light streams through the windows, enhancing the welcoming atmosphere.
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
A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.
Home in Whiting
4.84 out of 5 average rating, 152 reviews

The Spa of Downtown Whiting

SantiagoRating, 5 stars1 week ago
a really awesome place. I highly recommend this place.
Top guest favorite
A modern kitchen and dining area feature wooden cabinetry and a marble-topped island. A dining table with seating for eight is illuminated by overhead lighting. Windows allow for natural light, while a purple pendant light adds a pop of color to the space.
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
An inviting outdoor area features a wooden deck with a couch and a coffee table, surrounded by planters filled with vibrant flowers and greenery. Large windows provide a glimpse of the interior. A pergola overhead offers shade, enhancing the space's comfort and charm.
Home in Chicago
4.95 out of 5 average rating, 214 reviews

Paradise on the Park

LyndsayRating, 5 stars1 month ago
One of the best Airbnb’s I have stayed at! Super clear instructions, clean, modern, and a great location! I would definitely stay here again! I even had the opportunity to buy a piece of his original artwork 😊 The Airbnb is beautifully decorated in many of his original pieces and I was ecstatic to find out there were available to buy! Very communicative and friendly.

Private house rentals

Top guest favorite
The exterior of a historic house features a two-story facade with a gabled roof and large windows on the first level. Lush greenery surrounds the property, creating a welcoming atmosphere and enhancing the home’s charm.
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.
Superhost
A spacious living area is designed with high ceilings and natural light. Comfortable seating is provided by two leather sofas, while a wooden coffee table anchors the space. A large flat-screen TV is mounted on a dark accent wall, and subtle decor includes plants and wall art.
Home in Chicago
4.86 out of 5 average rating, 101 reviews

Casa PLZN Location | Entire Home | Garage Parking

RicardoRating, 5 stars2 weeks ago
Great place! I’ll definitely be coming back! The beds are amazing!
Top guest favorite
A game room features a felt-covered pool table, foosball table, and air hockey table against a backdrop of a beach scene mural. Orange-painted walls enhance the lively atmosphere. Several gray chairs are arranged neatly along one side of the room, providing ample seating.
Home in Elmhurst
5 out of 5 average rating, 46 reviews

Big Family Home with 4 King Beds

LauraRating, 5 stars1 week ago
We were a family of 14. My 3 adult Kids and their spouses, my 6 grandkids, ages 2 to 21 years old. The number of beds fit us comfortably. The game/activity room was a hit with the kids especially. The dining room and kitchen dinning areas fit us well. We did have some issues, that Syed responded to quickly. Syed is a very nice man and a great host, however the house is in need of some minor repairs, the garbage disposal didn’t work, cabinets in the kitchen need repair, we had ants on the counter in the kitchen that we had to spray to get rid of. The railing going upstairs was coming out of the wall. Syed responded quickly to rectify most of these things. The house and bathrooms are clean, but the tub and showers need to be recaulked, They are showing signs of mold. I spoke with Syed about these issues and he assured me they will be taking care of all these things. I believe that he will. Overall it was a great place for a large family. It met our needs for the 4 days we were there.
Superhost
The exterior of a three-story house is showcased, featuring a beige siding facade and a welcoming entrance with a white door. A balcony with railings is visible on the upper level, surrounded by clear blue skies and complemented by a small staircase leading to the front yard.
Home in Chicago
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars6 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
The image presents a two-story home with framed cedar bevel siding. A welcoming front porch features wooden railings and steps leading to the entrance. Surrounding greenery adds a natural touch, while the well-maintained pathway and lawn contribute to the property’s inviting exterior.
Home in Blue Island
4.81 out of 5 average rating, 194 reviews

Warm and comfortable inviting Suburban home !

MariaRating, 5 stars2 weeks ago
very nice and responsive house great peaceful calm area just a little bit far from the city with traffic otherwise wonderful stay, plan to book again !
Top guest favorite
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.94 out of 5 average rating, 124 reviews

Quiet cul-de-sac with huge fenced in backyard

JazzmenRating, 5 stars3 weeks ago
Tom and his dog Bear... were great!! Beautiful home and great area. A lot of places that we wanted to go to were close by will definitely come again. Thank for having such a welcoming home.
Superhost
A welcoming living room features a gray sofa opposite a wooden coffee table with a decorative bowl. Two armchairs sit beside a large window, providing natural light, while a television is positioned near a black fireplace. The warm-toned walls enhance the cozy atmosphere.
Home in Chicago
4.84 out of 5 average rating, 502 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

JamilaRating, 5 stars2 weeks ago
Beautiful home, clean, 3 min away from the green lane that takes you right to downtown Chicago, Calm neighborhood
Top guest favorite
A spacious ranch house is depicted, surrounded by matured trees and a well-maintained lawn. The facade features a combination of brick and siding, with a large garage and a welcoming front porch. Sunlight filters through the leaves, creating a serene atmosphere.
Home in Itasca
5 out of 5 average rating, 51 reviews

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

KellyRating, 5 stars1 month ago
We absolutely loved our stay with Jehu in Itasca! I grew up there in my childhood and her home made us feel so cared for and comforted. It is beautifully laid out, well appointed and so convenient for travelers that want to stay in the suburbs but have easy access to the city and airport. I plan to stay often when I return!

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