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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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
Apartment in Evanston
4.94 out of 5 average rating, 160 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the spacious, sunny 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 4 guests. The vintage kitchen is well supplied inc. Keurig & pods. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

Superhost
A spacious bed with a patterned quilt is featured in the foreground, accompanied by a decorative pillow. Soft lighting and neutral walls create a calming environment, while a cozy seating area and television are visible in the background.
Guest suite in Norwood Park
4.77 out of 5 average rating, 346 reviews

Spacious in-law Apt: 10 min to O'Hare and Downtown

Our family would love to share our in-law apt. (private entrance) in our Norwood Park house. A beautiful neighborhood, the convenience of O'Hare and the highway, and 3 ways to get downtown less than a mile away (blue line and metra). Great food, bars, grocery store, and parks all within walking distance. A great alternative to the hustle and bustle of the city but you can be in some of the best neighborhoods in the city in 15 min (Wicker Park, Lincoln Park, Logan Sq.) and downtown in 25.

Top guest favourite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Apartment in Evanston
4.97 out of 5 average rating, 537 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

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
4.98 out of 5 average rating, 280 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 stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.
Home in Evanston
4.87 out of 5 average rating, 200 reviews

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Top guest favourite
An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.
Townhouse in Evanston
5 out of 5 average rating, 114 reviews

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Guest favourite
A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.
Apartment in Maywood
4.94 out of 5 average rating, 189 reviews

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

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, 43 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.

Top guest favourite
The airy living room features a spiral staircase leading to the upper level. A wooden coffee table lies in front of a comfortable sofa. A vibrant vinyl record player sits atop a wooden crate, with bookshelves filled with various titles in the background. Natural light streams through multiple windows.
Guesthouse in Evanston
4.99 out of 5 average rating, 300 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Guest favourite
The exterior of a charming two-story house is presented, featuring a covered porch with white railings. The landscaped front yard includes flower beds, with a blue mailbox positioned nearby. A pathway leads to the entrance, framed by lush greenery under a blue sky dotted with clouds.
Apartment in Evanston
4.85 out of 5 average rating, 144 reviews

An awesom 2 Br apt. Evanston/close to NU & Loyola

Enjoy our cozy, newly rehabbed 2 bedroom apartment located in a quiet residential neighborhood. The unit is centrally located minutes from Northwestern University (1.5 mi), Loyola University (3.8 mi), Downtown Evanston, the Lakefront and Chicago. The apartment is perfectly sized for couples, families with small children, parents and teens on college visits or friends, and is equipped with essential amenities, free WIFI and TV.

Guest favourite
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
4.89 out of 5 average rating, 82 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!

Popular amenities for Skokie vacation rentals

When is the best time to visit Skokie?

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Avg. price$172 CAD$170 CAD$186 CAD$194 CAD$198 CAD$204 CAD$201 CAD$205 CAD$190 CAD$183 CAD$183 CAD$186 CAD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Skokie?

    Skokie has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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.

  • 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.

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

    Yes! Work meets play with ease at over 100 vacation rentals in Skokie featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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 280 vacation rentals in Lincolnwood, and over 520 vacation rentals in Skokie.

  • 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.

  • Do apartment rentals in Skokie have a kitchen?

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

  • 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.

  • 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.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with a kitchen, over 30 homes with free parking, over 40 homes with wifi, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Skokie

  • Total vacation rentals

    Explore 150 vacation rentals in Skokie

  • Nightly prices starting at

    Skokie vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 7,130 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    140 of Skokie vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Skokie rentals

  • 4.7 Average rating

    Skokie stays receive an average rating of 4.7 out of 5 from guests

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