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
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, 296 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 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, 116 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 favorite
Home in Skokie
4.95 out of 5 average rating, 80 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

Food has been known to being people together. Now is your chance to enjoy this lovely remodelled home with your friends and family in this quiet/safe north suburb of Chicago. With commercial grade appliances , we also offer you a pizza oven, smoker and regular BBQ to be able to cook some spectacular meals together in the custom built cooking station. Concerned about parking? We have a 90ft driveway that will be sure to fit most of your cars along with free street parking conveniently located!

Top guest favorite
A living area features natural light from multiple windows, complemented by a ceiling fan. A comfortable sofa with textured throws faces a modern fireplace. Two brown armchairs are positioned nearby, and a decorative rug lies under a coffee table, which displays a potted plant and a magazine.
Apartment in Evanston
4.99 out of 5 average rating, 102 reviews

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Guest favorite
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, 104 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 favorite
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, 164 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

Guest favorite
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, 209 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
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 241 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Guest favorite
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
4.93 out of 5 average rating, 149 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 favorite
Home in Skokie
4.89 out of 5 average rating, 18 reviews

Comfy Cove: 3BR-2BT *NEW* w/ 2 Living Rooms

Welcome to our cute and cozy 3BR, 2BT home in Skokie—the perfect blend of comfort and convenience. Thoughtfully designed- this space is ideal for families, friends, or business travelers. Enjoy comfortable bedrooms, a fully equipped kitchen, and relaxing living areas that make you feel right at home. Located in a quiet neighborhood with easy access to Chicago, dining, shopping, and local attractions. Whether you’re here for a weekend getaway or an extended stay, this is the place.

Guest favorite
The historic home exterior is showcased, featuring a vibrant red facade with white accents. A charming porch adorned with lattice and railings provides an inviting entrance. Lush greenery surrounds the property, complemented by a white picket fence and vibrant landscaping.
Apartment in Wilmette
4.9 out of 5 average rating, 288 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Top guest favorite
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, 211 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.

Popular amenities for Skokie vacation rentals

When is the best time to visit Skokie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ463ﺩ.ﺇ455ﺩ.ﺇ499ﺩ.ﺇ521ﺩ.ﺇ533ﺩ.ﺇ547ﺩ.ﺇ540ﺩ.ﺇ551ﺩ.ﺇ510ﺩ.ﺇ492ﺩ.ﺇ492ﺩ.ﺇ499
Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°C-1°C

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

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 ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 6,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 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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