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, 70 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.

Top guest favorite
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, 178 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.

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
A comfortable living space features a dark leather couch adorned with patterned throw blankets. Two side tables stand adjacent to the couch, and a coffee table occupies the center of the room. Natural light filters through two windows, brightening the area.
Apartment in Evanston
4.94 out of 5 average rating, 161 reviews

Cute & comfortable apartment on quiet street

Rest and relax at this peaceful, cozy & comfortable upstairs apartment located in a quiet, family-friendly neighborhood surrounded by local parks & tree lined streets. It's a short distance to restaurants, the lakefront, and Northwestern University. There is easy parking and it's a short walk to public transit, to other local universities, Ryan Field, Welsh Ryan Arena, Downtown Chicago, Wrigley Field, and many museums, and concert venues. Note: laundry is only available to long term guests.

Top guest favorite
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, 531 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 favorite
The open-concept living area features modern furnishings, including two armchairs and a circular coffee table. A large television is mounted on the wall, complemented by dark shelving displaying decorative items. The dining area, visible in the background, is set with a table and chairs, all illuminated by soft lighting.
Home in Skokie
4.93 out of 5 average rating, 90 reviews

Peaceful Stay North Shore Escape | 8 Beds (2 King)

Enjoy this light-filled home in a quiet, tree-lined North Shore neighborhood. Just 10 minutes to Northwestern University and Lake Michigan, with easy access to Chicago—it’s the perfect place to unwind. Two king beds, a rooftop deck, and artful murals set a memorable backdrop for your stay. The open living space and well-equipped kitchen are ideal for meals, game nights, or relaxing. Nearby, discover shops and local dining favorites. A top choice for group getaways and seasonal escapes.

Top guest favorite
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, 271 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 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
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
4.86 out of 5 average rating, 187 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 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, 36 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
An inviting collage displays the exterior view of a charming house with a well-maintained lawn surrounded by lush greenery. Adjacent images highlight a game room featuring a pool table and a cozy movie room. A comfortable seating area is visible, alongside an outdoor patio space.
Home in Skokie
4.87 out of 5 average rating, 39 reviews

Urban Oasis | Kid Friendly | Quiet Street

Spacious rooms, cool design house, and peaceful location, ... are some of the things you can expect when staying at the property :). We also have tons of amenities: + game room for adults and kids + movie room HD projector + poker table + king bed + private garage & easily accessible street parking + many more... Distances: _ 5 minutes drive to Dempster train station. _ 7 minutes drive to Westfield Old Orchard mall. _ 25 minutes drive to down

Top 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, 100 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.

Popular amenities for Skokie vacation rentals

When is the best time to visit Skokie?

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Avg. priceR2,152 ZARR2,118 ZARR2,323 ZARR2,426 ZARR2,477 ZARR2,545 ZARR2,511 ZARR2,562 ZARR2,374 ZARR2,169 ZARR2,050 ZARR2,186 ZAR
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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 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 Apartment Rentals in Skokie?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with air conditioning, over 30 homes with free parking, over 30 homes with wifi, 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 vacation rentals in Skokie

  • Total vacation rentals

    Explore 140 vacation rentals in Skokie

  • Nightly prices starting at

    Skokie vacation rentals start at R512 ZAR 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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