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Holiday rentals 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
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.
Flat in Chicago
5 out of 5 average rating, 75 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 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 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!

Superhost
Home in Evanston
4.56 out of 5 average rating, 25 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

Guest favourite
Flat in Skokie
5 out of 5 average rating, 11 reviews

30-Nights Minimum Stay 3BR 2Car Driveway Parking

Furnished w/ comfy beds, living room seatings & well-stocked kitchen with Bosch mixer newly added in time for the holidays! 3-BR APT, adjacent to Lee Park, with 6x5 outdoor STORAGE SHED! Driveway PARKING is dedicated to unit. Skokie is a safe neighboring suburb to Chicago and Evanston. Yellow line/L train and bus stations are half mile away. 1-2 miles from Aldi, Oakton Market, Jewel-Osco, Target, Skokie library, Orchard mall, theaters & restau, walk/bike path.

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
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
4.87 out of 5 average rating, 105 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.

Superhost
The exterior of a modern house is shown, featuring a brick façade with large windows that provide ample natural light. A manicured lawn surrounds a concrete pathway leading to the entrance, framed by greenery. The roof is topped with gray shingles.
Home in Skokie
4.88 out of 5 average rating, 89 reviews

Cozy Home in Skokie

Modern, Cozy 2 bed 2 bath house in Skokie Find a home away from home in this newly renovated house. Only a short drive from the beautiful lakeside and NW Univ; it is perfect for all of your getaways. The property is within walking distance of a CVS pharmacy and is minutes away from a bus station. Train station is 7 min away and downtown is 30 min drive. Parking available on side street. shopping, restaurants and other popular locations.

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
Flat in East Rogers Park
5 out of 5 average rating, 6 reviews

Pristine 2BD|2.5BD Duplex| Chicago| Free Parking

Discover comfort and privacy in our stylish duplex apartment just steps from Lake Michigan. This 2-bedroom, 2.5-bath home features a spacious layout with the primary bedroom and ensuite bath on the upper level for added privacy. Enjoy a fully equipped kitchen, cozy living area, and high-speed WiFi. Unwind on the private back porch or explore downtown with ease thanks to nearby public transit. Perfect for both work and leisure

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!

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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