Holiday houses in Skokie

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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.
Apartment in Evanston
4.96 out of 5 average rating, 279 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!

Top Guest favourite
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, 27 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!

Guest favourite
The living area features a comfortable sofa adorned with patterned cushions, accompanied by a stylish coffee table. A modern dining setup is visible in the background, along with sleek kitchen cabinetry. Light from overhead fixtures illuminates the open layout with dark hardwood flooring.
Condo in Evanston
4.96 out of 5 average rating, 107 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Joy of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, outdoor pool, BBQ and picnic area and beautiful landscaping. Guests can enjoy the Clark Street Beach & Lighthouse

Guest favourite
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
4.95 out of 5 average rating, 42 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 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 modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Apartment in Lake View
4.95 out of 5 average rating, 150 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

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.
Apartment in Skokie
4.89 out of 5 average rating, 690 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!

Superhost
A well-lit bedroom is furnished with a spacious bed draped in crisp white linens. Two windows provide natural light, and a small desk with a black chair is positioned against one wall. Art pieces add a touch of character to the neutral-toned space.
Apartment in Skokie
4.88 out of 5 average rating, 78 reviews

Charming 2 bed/1 bath apt- walk 2 train/store/rest

Cozy 2 bedroom apartment. Quiet neighborhood. Spacious kitchen. Stroll over to any of the cute cafes and restaurants around or take a walk or run on the trail at the end of the block over to the local craft brewery. Multiple parks with playgrounds, nature trails, supermarkets and restaurants without having to cross a single large street. Even a train stop, all under 3 blocks away!

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.
Condo in Evanston
4.78 out of 5 average rating, 675 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$218 NZD$215 NZD$235 NZD$246 NZD$251 NZD$258 NZD$255 NZD$260 NZD$241 NZD$220 NZD$208 NZD$222 NZD
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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 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 500 vacation rentals in Skokie, over 90 vacation rentals in North Evanston, and over 260 vacation rentals in Lincolnwood.

  • 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 a kitchen, over 80 homes with wifi, over 80 homes with air conditioning, over 60 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Skokie have wifi?

    Absolutely! We offer over 80 house 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 $52 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Skokie holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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