House vacation rentals in Skokie

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Popular amenities for Skokie 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 stars4 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.
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 stars4 days 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 stars4 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 spacious basement area features a glass dining table surrounded by wooden chairs. The entertainment area includes a large sectional sofa and two wall-mounted televisions. A staircase leads to the upper level, while a gym space is visible to the right.
Home in Bartlett
4.64 out of 5 average rating, 25 reviews

Fully Furnished Executive Home, Lux Amenities

ApaviaRating, 5 stars2 months ago
From the time of booking until we checked in, our host Kevin was amazing!!! He was very responsive and very accommodating. Being at this location was so peaceful and felt like a home away from home. I look forward to booking with Kevin again in the future. Highly recommended
The exterior of a three-story townhome is presented, featuring light-colored siding and a brick accent. A single-car garage is visible, along with a small front lawn. Large windows allow natural light to enter, while a tree branch extends above, casting gentle shadows.
Home in Schaumburg
4.71 out of 5 average rating, 7 reviews

Spacious 3 Floor Townhome

MelissaRating, 5 stars2 weeks ago
This spot is awesome. Close to the mall and lots of places to eat and things to do. Very spacious tri level. Free Parking on premises. Lots of room for people to sleep very spacious. Comfy couches. The bed I had was great. Our venue was very close for the event we attended we will be back!
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, 47 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars1 week 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 stars2 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 stars7 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.

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 Roscoe Village
4.92 out of 5 average rating, 280 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars2 weeks ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
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, 147 reviews

Home in Glen Ellyn

KellyRating, 5 stars1 week ago
We enjoyed our night here. It provided a calm place to rest and plenty of space. Host was wonderful to work with.
Guest favorite
Home in Wicker Park
4.98 out of 5 average rating, 152 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Kevin And CourtneyRating, 5 stars1 month 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 Wicker Park
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 Avondale
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 stars3 days 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 Lake View
4.95 out of 5 average rating, 183 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 West Town
4.95 out of 5 average rating, 214 reviews

Paradise on the Park

LyndsayRating, 5 stars3 weeks 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 stars3 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.
Guest favorite
A modern kitchen features grey cabinetry and stainless steel appliances, including a microwave, oven, and refrigerator. A granite countertop provides ample space for food preparation. Soft lighting illuminates the area, enhancing functionality and comfort.
Home in Schaumburg
4.96 out of 5 average rating, 55 reviews

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

AmyRating, 5 stars1 month ago
Our team enjoyed their stay while there for a work trip. Would definitely book again!
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 Illinois Medical District
4.86 out of 5 average rating, 99 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars3 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Guest favorite
Home in Logan Square
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
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 Austin
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.
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
4.93 out of 5 average rating, 123 reviews

Quiet cul-de-sac with huge fenced in backyard

MichaelRating, 5 stars3 weeks ago
Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again
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 Near West Side
4.84 out of 5 average rating, 501 reviews

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

JamilaRating, 5 stars1 week 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!

Quick stats about house rentals in Skokie

  • Total rentals

    80 properties

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 properties include access to wifi

Destinations to explore

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  5. Skokie
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