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Holiday rentals in Skokie

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Skokie

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

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Top guest favourite
The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.
Home in Wilmette
4.98 out of 5 average rating, 184 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Top guest favourite
The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.
Flat in Evanston
4.96 out of 5 average rating, 280 reviews

Stylish & Comfy Gem near Downtown~Balcony~Parking

My 2nd floor, 2 BD/1BA home sits in a quiet cul-de-sac, about 1 mi from downtown Evanston. A 15-min walk to the Dempster Purple line station, which brings you right into Chicago. Northwestern and Loyola are nearby for a visit too! The area has wonderful lakeside parks and beaches, so no matter the time of year, you'll appreciate the natural beauty! Grocery stores, coffee shops, and restaurants are within walking distance as well. -Electric Fireplace -Fully Equipped Kitchen -Queen Sized Bedrooms

Guest favourite
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, 115 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 favourite
The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.
Guest suite in Evanston
4.97 out of 5 average rating, 276 reviews

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Guest favourite
A spacious sleeping area features a large bed topped with neutral-toned linens and decorative pillows. Two bedside lamps provide soft lighting beside nightstands. A plush rug adds warmth to the floor, and a comfortable chair is positioned in the corner under a world map wall decor.
Flat in East Rogers Park
4.85 out of 5 average rating, 129 reviews

Parking & In-Unit Laundry & Now a King Bed!

Located in wonderful West Ridge, this is a private garden/basement apartment with only 6 steps down. Separate entrance, as well as in-unit washer and dryer. You’ll have your very own parking on premises in back. 5 Minute walk to: - Famous Devon Ave for delicious cultural cuisine - Fresh Markets - Bus stops 5 - 10 Minute drive to: - The beach - Groceries (Jewel Osco, Food For Less, Mariano’s) - Indian Boundary Park - Target, Walmart - Long Horn, Olive Garden Red Lobster & more

Superhost
A modern galley kitchen features green cabinetry and white countertops. A decorative backsplash with a floral pattern complements the design. Appliances include a gas stove, dishwasher, and coffee maker, while ample shelving showcases houseplants and decorative items.
Flat in Logan Square
4.85 out of 5 average rating, 179 reviews

Funky & newly remodeled 1 bed in Hip Logan Square

Recently remodeled 1 bedroom garden apartment with a fun aesthetic in hip Logan Square. Walking distance to top bars, restaurants and coffee shops such as Sugarmoon, Park & Field, Best Intentions, Lou Malnatis, Damn Fine Coffee Bar and many more. Blocks from the 606 Trail, 90/94 & public transportation. Lovely shared front yard landscaped with florals + garden beds. We will pass along a welcome guide with a list of all our favorite places in the neighborhood!

Guest favourite
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
4.96 out of 5 average rating, 103 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 favourite
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.
Flat in Skokie
4.89 out of 5 average rating, 691 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!

Guest favourite
A modern living area features a comfortable sofa adorned with patterned cushions and a golden throw. A wooden coffee table sits in front, complemented by a minimalistic television stand. Light from a floor lamp brightens the space, while potted plants add a touch of greenery.
Flat in Albany Park
4.95 out of 5 average rating, 112 reviews

Bright Apartment

Relax in this sunny one-bedroom garden apartment in Albany Park (Not recommended for taller than 6'3"). Our apartment is perfectly located between downtown Chicago & O'Hare airport. You can go just about anywhere in the city in about 20-30 min as we are 5 minutes away from the Montrose blue line train stop, Kimball brown line train stop, and the I90/94 interstate. Please note, some areas have lower soffit ceilings.

Top guest favourite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Apartment in Lake View
4.99 out of 5 average rating, 669 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Top guest favourite
A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.
Guest suite in Portage Park
4.96 out of 5 average rating, 144 reviews

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Guest favourite
A modern multi-story building is nestled among leafy trees, featuring large windows and a sleek, minimalistic design. A wooden staircase leads to the entrance, while blooming flowers add a touch of color to the landscaped garden in front.
Apartment in Evanston
4.78 out of 5 average rating, 676 reviews

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

Popular amenities for Skokie holiday rentals

When is the best time to visit Skokie?

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Avg. price$162 SGD$159 SGD$175 SGD$182 SGD$186 SGD$191 SGD$189 SGD$193 SGD$179 SGD$163 SGD$154 SGD$164 SGD
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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 apartment rentals in Skokie have a kitchen?

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

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

    Experience the best of Skokie with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Skokie have air conditioning?

    Absolutely! We offer over 80 house 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 260 vacation rentals in Lincolnwood, over 90 vacation rentals in North Evanston, and over 500 vacation rentals in Skokie.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Skokie have wifi?

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

Quick stats about holiday rentals in Skokie

  • Total holiday rentals

    Explore 140 holiday rentals in Skokie

  • Nightly prices starting at

    Skokie holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,800 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    130 of Skokie holiday rentals include wifi 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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