Holiday houses 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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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, 117 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.

Guest favourite
A shaded outdoor deck features comfortable seating arrangements with deep blue cushions. A wooden coffee table occupies the center, while a grill is positioned at one side. Soft lighting enhances the cozy atmosphere as the sun sets in the background.
Home in Skokie
4.89 out of 5 average rating, 108 reviews

Luxe Limewash Getaway w/Sun Deck

Relax with the whole family at this peaceful place to stay! This retreat seamlessly blends classic charm with modernity. Enjoy a cozy living room, bonus piano space, and new bathrooms. Relax on the deck or explore nearby gems. Conveniently near highways, it's an ideal hub to explore Skokie, Evanston, Niles, Wilmette, Evanston, and Chicago. O'Hare Airport - 25 min drive Wrigley Field - 12 min drive Northwestern University - 9 min drive Loyola University - 9 min drive Starbucks ‬- 3 min drive

Guest favourite
A modern kitchen and dining area are presented, featuring a sleek island with bar stools and a dining table with six chairs. Natural light is provided by large windows, and contemporary fixtures enhance the space's functionality and design.
Apartment in Evanston
4.91 out of 5 average rating, 173 reviews

New 3bd/1.5 bth Apt w/private prkg

A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

Top Guest favourite
The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.
Guesthouse in Evanston
5 out of 5 average rating, 86 reviews

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

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
4.86 out of 5 average rating, 218 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.

Guest favourite
A modern living area is presented, featuring a comfortable sectional sofa adorned with yellow accent pillows. A large flat-screen Smart TV is mounted on the wall, providing entertainment options. Natural light filters through the window, highlighting the warm wood flooring.
Apartment in Evanston
4.94 out of 5 average rating, 154 reviews

NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU

Relax with the whole family or explore the city at this peaceful newly renovated 3bd/1bth apartment with plenty of free parking and in-unit washer/dryer. You’ll be close to everything when you stay at this centrally-located place. Only 2 mins from DT Evanston and 25 mins from DT Chicago! Just mins away from Northwestern and Loyola Universities. Enjoy the 65in and 55in Smart TVs, listen to your favorite tunes w/ the voice enabled Amazon Echo Alexa speaker, or enjoy family games.

Guest favourite
A comfortable living room features a blue sectional sofa adorned with soft throws, paired with a wooden coffee table. Natural light enters through large windows, highlighting a stylish armchair and an entertainment unit beneath a mounted TV.
Apartment in Evanston
4.9 out of 5 average rating, 131 reviews

Guest Favorite Escape Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Explore nearby beaches, stroll along the lakefront, and discover vibrant downtown shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable Evanston getaway!

Top Guest favourite
The spacious bathroom features a freestanding tub and a glass-enclosed shower. A large mirror with a decorative frame is mounted on one wall. The floor is covered with a patterned rug, complementing the warm wall color and wood flooring.
Apartment in Evanston
4.97 out of 5 average rating, 213 reviews

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.93 out of 5 average rating, 111 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Guest favourite
A spacious living area features plush blue sofas and a round marble coffee table. A large television is positioned on a wooden stand, while a modern kitchen with a breakfast bar is visible in the background. Natural light illuminates the space, enhancing its inviting atmosphere.
Home in Skokie
4.88 out of 5 average rating, 33 reviews

Stokes Stay: Stunning 4BR/2.5BT

Welcome to Stokes 🌟 You’ll be stoked to be here! This spacious 4-bedroom, 3-bath ranch home offers modern finishes, 4 king-sized beds, and plenty of room to relax or entertain. With a fully fenced yard, cozy lounge spaces, and a finished basement game room, it’s the perfect spot for families, friends, or business travelers—just minutes from Skokie’s restaurants, shopping, and a quick drive to downtown Chicago.

Guest favourite
A bright living area features a modern design with large windows allowing natural light. Two armchairs are positioned near a white coffee table, complemented by a leather sofa draped with a soft throw. Light-colored curtains frame the windows, creating a soft ambiance.
Home in Skokie
4.93 out of 5 average rating, 83 reviews

Luxury Home - Pool Tbl/Bar/Patio

This unique place has a style all its own. Fully remodelled to wow you and your guest! Cozy, yet spacious environment for you and your friends to rest, cook, play pool by the bar or sit outside in the patio with a wood fire! You will be extremely close to downtown Chicago, O’Hare airport, Wrigley Field, many shopping attractions all while being in a safe neighborhood. Easy self checkin process!

Top Guest favourite
A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.
Condo in Evanston
4.95 out of 5 average rating, 130 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

Popular amenities for Skokie holiday rentals

When is the best time to visit Skokie?

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Avg. price$190 AUD$193 AUD$210 AUD$199 AUD$203 AUD$208 AUD$206 AUD$210 AUD$194 AUD$187 AUD$187 AUD$190 AUD
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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 50 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 90 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 270 vacation rentals in Lincolnwood, and over 530 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 house rentals in Skokie have a kitchen?

    Absolutely! We offer over 70 house rentals with a kitchen in Skokie. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Skokie have wifi?

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

  • Do house rentals in Skokie have free parking?

    Absolutely! We offer over 60 house 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 30 homes with free parking, over 40 homes with wifi, over 30 homes with air conditioning, over 40 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 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, 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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