Vacation rentals in Skokie

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Top-rated vacation rentals in Skokie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in Chicago
5 out of 5 average rating, 65 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Guest favorite
A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.
Home in Skokie
4.95 out of 5 average rating, 113 reviews

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

Top guest favorite
The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.
Guesthouse in Evanston
5 out of 5 average rating, 64 reviews

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

Guest favorite
A living area is adorned with midcentury modern furnishings, including a patterned green armchair and a dark, decorative coffee table. A television is mounted on an entertainment unit, while a dining area is visible in the background, featuring a round table with chairs and a sideboard.
Home in Skokie
4.96 out of 5 average rating, 25 reviews

Unique and Historic Lustron Home

Take a trip back to the 50s! This is a fascinating 2 Bedroom Lustron Home built in 1949 is decorated with midcentury modern flair. You will marvel at this home's 100% steel materials and construction including walls, ceilings, cabinets, pocket doors, interior and exterior. The pictures are hung with magnets! You will love the comfort and coziness along with the atomic age style and flair. The yard has both a badminton and croquet sets. There is also an outside patio dining area. Enjoy!

Superhost
Home in Evanston
4.88 out of 5 average rating, 8 reviews

2BR Coach House w/ Patio + Parking | Evanston

We are excited to welcome you to this charming and spacious apartment if you're visiting Evanston/Chicago. We are very close to Northwestern University, Downtown Evanston and Lake Michigan. Working, relaxing, living. Our space has all the other essentials you need for your stay. - Contact-free check-in - 24/7 virtual support - Xfinity Wi-Fi - Fresh towels and bathroom essentials - Pre-cleaning before your arrival - Fully equipped kitchen - NETFLIX and HDMI for streaming

Top guest favorite
The exterior of a two-story brick house features white shutters and a welcoming dark blue front door. A covered porch is visible above the entrance, flanked by two large windows. Lush greenery and a manicured lawn enhance the inviting appearance of the home.
Home in Skokie
5 out of 5 average rating, 34 reviews

House in Skokie-Your Cozy Home Away from Home!

Welcome to your cozy house in Skokie - just a short drive to the heart of Chicago, the lakefront, Northwestern and Loyola - making it an ideal spot for whatever brings you to the area! This warm and inviting 2-bedroom, 1.5-bath home is perfectly situated for those wanting to explore the city while enjoying a peaceful retreat in the suburbs. Whether you're here for a weekend getaway or an extended stay, you’ll find everything you need to feel right at home.

Guest favorite
The exterior of a charming two-story home is featured, surrounded by well-maintained landscaping. A pathway made of pavers leads to the front entrance, framed by vibrant green shrubs and trees. The house showcases a gabled roof with dormer windows and yellow front door.
Home in Skokie
4.86 out of 5 average rating, 102 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

20 mins from popping downtown Chicago and tucked within one of the Northside’s finest tree-line streets—The Haus of Love: A modern wood burning fireplace, new hardwood floors, and a bright airy space greets you in this newly renovated Kosher inspired design Spacious Eat-In Kitchen w/ double everything. Separate Formal Dining. Wetbar. High End Quartz Countertops 3Bd 3.5Bath Master BD w/Heated Floors, 10-ft ceiling, skylights, and a huge 8-ft tub.

A comfortable living area features a dark sofa paired with a light coffee table atop a patterned rug. A flat-screen television sits on a low console, with a floor lamp providing soft light. A small potted plant adds a touch of greenery to the space.
Apartment in Skokie
4.76 out of 5 average rating, 25 reviews

Skokie Gem - 1BR on Davis St!

Explore Skokie and Chicago from this ideally located 1-bedroom apartment on Davis St. Enjoy the convenience of nearby public transportation, making it a breeze to reach downtown Chicago, Northwestern University, and other popular destinations. This comfortable unit features a private bedroom, a full bathroom, and a functional living space. Whether you're here for work or leisure, this Skokie gem offers a fantastic base for your travels.

Guest favorite
A spacious living room is furnished with a large sectional sofa and vibrant cushions. A glass coffee table is centered, surrounded by decorative flowers. Soft lighting enhances the neutral walls, while a landscape painting adds a touch of color. Large windows allow natural light to fill the space.
Home in Skokie
4.97 out of 5 average rating, 98 reviews

*King Bed-Updated-Laundry-Near NWU-Hospitals+More

Enjoy complete privacy in our newly updated home. We live downstairs, and you have a total privacy on the main level of our spacious home with 3 bedrooms, 1 bathroom, full kitchen, and shared laundry. We provide you with all the amenities you need for a comfortable trip. Our home is minutes from Evanston, Northwestern University, Lake Michigan lakefront, beaches, several hospitals, and lots of shopping and restaurants. NO PARTIES.

Guest favorite
A spacious living area is visible, featuring a comfortable seating arrangement with two sofas and a round coffee table. A large television is positioned on a stand across from the seating. The kitchen area, accessible through an open entry, showcases modern appliances and dining seating.
Apartment in Skokie
4.89 out of 5 average rating, 682 reviews

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

Top guest favorite
A spacious basement suite is shown with a combination of seating and sleeping areas. A comfortable bed is paired with a dark entertainment unit and a large wall-mounted TV. The decor includes a patterned rug and various accent pieces, providing a cozy and functional environment.
Guest suite in Morton Grove
4.96 out of 5 average rating, 27 reviews

Cozy Garden Suite with Kitchen

Private basement suite with separate entrance. -Plenty of free street parking. -Near I-94 expressway. -Within walking distance to many restaurants and 5 minute drive to grocery stores. -Metra train within walking distance. -Bus which goes to O’hare and Evanston within walking distance. -Full kitchen -Washer and dryer Non-smoking house. No parties. No extra guest visits unless agreed upon prior.

Top guest favorite
The open living area features a spacious sectional sofa facing a modern stone fireplace. A wall-mounted smart TV is visible above the fireplace, while a kitchen island with bar seating is positioned nearby. Natural light enters through windows, enhancing the neutral decor.
Home in Skokie
5 out of 5 average rating, 31 reviews

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

Welcome to CASA 22 Exquisite 3-bedroom, 2-bathroom luxurious home, combines contemporary decor with modern amenities and an experience all can enjoy!A beautiful staircase leads in a fully furnish cozy basement.This property it’s situated in a very desirable neighborhood and prime location.Our goal its to provide a 5 star experience during your stay in this property.

Popular amenities for Skokie vacation rentals

When is the best time to visit Skokie?

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Avg. priceﺩ.ﺇ463ﺩ.ﺇ455ﺩ.ﺇ499ﺩ.ﺇ521ﺩ.ﺇ533ﺩ.ﺇ547ﺩ.ﺇ452ﺩ.ﺇ444ﺩ.ﺇ466ﺩ.ﺇ441ﺩ.ﺇ441ﺩ.ﺇ470
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Skokie?

    Skokie has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Skokie?

    Yes! Work meets play with ease at over 90 vacation rentals in Skokie featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Skokie have free parking?

    Absolutely! We offer over 30 apartment rentals with free parking in Skokie. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Skokie?

    Four-legged friends are welcome in Skokie. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Do house rentals in Skokie have a kitchen?

    Absolutely! We offer over 70 house rentals with a kitchen in Skokie. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Skokie?

    Experience the best of Skokie with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Skokie have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Skokie. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Skokie?

    Make yourself at home in Skokie by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in North Evanston, over 390 vacation rentals in Wildwood, and over 500 vacation rentals in Skokie.

  • What are the most popular amenities for House Rentals in Skokie?

    Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with wifi, over 70 homes with a kitchen, over 70 homes with air conditioning, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Skokie have wifi?

    Absolutely! We offer over 40 apartment rentals with wifi in Skokie. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Skokie

  • Total vacation rentals

    Explore 140 vacation rentals in Skokie

  • Nightly prices starting at

    Skokie vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 6,800 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Skokie vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Skokie rentals

  • 4.8 Average rating

    Skokie stays are highly rated by guests—averaging 4.8 out of 5!

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