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Holiday houses 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
The open living area features a spacious sectional sofa facing a modern stone fireplace. A wall-mounted smart TV is visible above the fireplace, while a kitchen island with bar seating is positioned nearby. Natural light enters through windows, enhancing the neutral decor.
Home in Skokie
5 out of 5 average rating, 42 reviews

Casa 22 Luxury & Modern 3BD 2BA Home in Skokie

Welcome to Casa 22! Our spacious 3-bedroom, 2-bath home in Skokie, Illinois — perfectly designed for groups, families, or business travelers. With room for up to 6 guests, this home combines contemporary décor with thoughtful amenities for a comfortable stay. Located in a prime Skokie neighborhood near shopping, dining, and transit, you’re just minutes from O'hare Airport and Downtown Chicago. Whether you’re here for work or play, this home offers a serene stay with easy access to everything th

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, 119 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, 111 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, 185 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, 92 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.

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, 542 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.

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, 228 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, 160 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.

Superhost
Home in Skokie
4.77 out of 5 average rating, 30 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 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, 134 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, 216 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.

Superhost
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
4.88 out of 5 average rating, 86 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 holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Skokie

An open plan kitchen is visible, featuring a modern stainless steel refrigerator and a countertop adorned with a decorative blue centerpiece. The living and dining areas are well-lit, showcasing comfortable seating and large windows that look out to the street.
Home in Skokie
4.82 out of 5 average rating, 113 reviews

Quiet and welcoming house.

Guest favourite
The exterior of a historic apartment building is displayed, featuring a spacious front porch with wooden railings and a staircase leading to the entrance. Lush green grass surrounds the property, with a few carved decorations visible on the steps.
Home in Skokie
4.87 out of 5 average rating, 95 reviews

A+amazing beauty, entire 2 BR Skokie historic stay

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, 110 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

A comfortable living area features a dark sofa paired with a light coffee table atop a patterned rug. A flat-screen television sits on a low console, with a floor lamp providing soft light. A small potted plant adds a touch of greenery to the space.
Apartment in Skokie
4.66 out of 5 average rating, 41 reviews

Skokie 1BR Stay Near Parks, Dining & Transit

Guest favourite
The exterior of a welcoming home is shown, featuring a light-colored stone facade and a neatly manicured front yard. A curved walkway leads to the front door, which is framed by a large tree providing shade. The overall setting is calm and suburban.
Home in Skokie
4.86 out of 5 average rating, 88 reviews

Cozy, sun drenched, spacious, perfect location!

Top Guest favourite
A modern living area features large windows providing abundant natural light and views of the surrounding landscape. Two light gray sofas are arranged around a circular glass coffee table, while an orange accent chair adds a pop of color. A tasteful wall art piece complements the contemporary décor.
Apartment in Evanston
4.98 out of 5 average rating, 54 reviews

"Hope of Evanston" 2BDR/2BTH

Top Guest favourite
Guesthouse in Evanston
5 out of 5 average rating, 20 reviews

Welcome to Serenity.

A comfortably arranged bedroom features a plush king-size bed with gray bedding and decorative pillows. Two side tables with lamps sit beside the bed, and a flat-screen TV is mounted on the wall. A modern bench and a small armchair add functionality to the space.
Apartment in Skokie
4.81 out of 5 average rating, 26 reviews

Lovely 1BR Apt w/ WiFi | Peaceful & Central Stay

When is the best time to visit Skokie?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$194 AUD$197 AUD$214 AUD$203 AUD$207 AUD$213 AUD$210 AUD$214 AUD$198 AUD$191 AUD$191 AUD$194 AUD
Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°C-1°C

Frequently Asked Questions

  • What are the best things to do in Skokie with kids?

    Kids enjoy interactive exhibits at the Illinois Holocaust Museum, nature exploration at Emily Oaks Nature Center, and creative play in local parks or splash pads. Community events and craft programs add options for family outings year round.

  • What are some of the best things to do in Skokie?

    Explore the exhibits at the Illinois Holocaust Museum, walk through landscape trails at Emily Oaks Nature Center, and discover public art installations in Skokie Northshore Sculpture Park. Downtown Skokie has eateries, shops, and community events.

  • How is the weather in Skokie?

    Skokie has cold winters around 19–32°F (−7–0°C) and warm summers near 66–85°F (19–29°C), with moderate rainfall throughout the year. Spring and autumn bring milder temperatures, so pack layered clothing to adjust with the seasons.

  • When is the best time to visit Skokie?

    Late spring and early autumn are often recommended for comfortable temperatures, blooming parks, and seasonal community events. Summer appeals to visitors with outdoor festivals, farmer’s markets, and longer daylight hours.

  • What are the best places to visit in Skokie?

    Explore the Illinois Holocaust Museum and Education Center, stroll through Emily Oaks Nature Center, and discover artistic exhibits at the Skokie Northshore Sculpture Park. Downtown Skokie has shops, eateries, and locally organized events.

  • What are some hiking trails in Skokie?

    Emily Oaks Nature Center has short trails ideal for leisurely walks and wildlife spotting. The Skokie Northshore Sculpture Park features paved paths surrounded by art installations and greenery.

  • What are some family activities we can do in Skokie?

    Families explore hands-on exhibits at the Illinois Holocaust Museum’s youth area, take nature walks at Emily Oaks Nature Center, and visit playgrounds or splash pads in local parks. Community centers often feature inclusive programs and seasonal activities.

  • What are some of the best day trip ideas from Skokie?

    Explore botanical gardens and vibrant neighborhoods in the surrounding area, or visit Chicago for world-renowned museums, architecture, and lakefront walks. Nature lovers often head to nearby forest preserves and scenic parks.

  • Are there any pet friendly accommodations available in Skokie?

    Skokie has pet friendly vacation rentals, especially in residential neighborhoods and near parks. Many stays welcome dogs, making it convenient to visit nearby walking trails or green spaces.

  • What are some local tips for visiting Skokie?

    Explore Skokie’s mix of cultural centers, parks, and dining spots reflecting the town’s diversity. Dress in layers, as temperatures vary throughout the year, and try connecting with locals for recommendations on distinct food or hidden park spots.

  • What is Skokie known for?

    Skokie is known for its diverse community, cultural institutions, and locally rooted culinary scene. The Illinois Holocaust Museum highlights education and remembrance, while green spaces invite nature exploration.

  • What are the best hidden gems to explore in Skokie?

    Emily Oaks Nature Center is frequently suggested for quiet walks and pond views, while local bakeries and multicultural markets showcase distinct flavors and traditions. Community gardens and neighborhood parks around Skokie provide relaxed spaces off the main routes.

  • What are the best foods to try in Skokie?

    Skokie has vibrant flavors, often featuring locally rooted Jewish delicatessens, Eastern European bakeries, and Middle Eastern restaurants. Try dishes like falafel, fresh bagels, and savory pierogies; multicultural markets also highlight diverse snacks and sweets.

  • What should I bring for a trip to Skokie?

    Pack comfortable walking shoes, layers for shifting temperatures, and a rain jacket or umbrella, especially in spring or autumn. A reusable water bottle and sunscreen are helpful for time spent in parks or outdoor spaces.

  • What is the nightlife in Skokie like?

    Skokie has casual nightlife, with locally rooted bars, relaxed lounges, and family-friendly venues for evening gatherings. For more lively options, many visitors explore nearby urban areas known for music, comedy, and diverse bites.

  • What are the most popular events or festivals in Skokie?

    Skokie Festival of Cultures is often recommended in late spring, with food, music, and performances reflecting the town’s diversity. Summer brings farmer’s markets and community fairs, while holiday parades brighten the winter season.

  • Are there family friendly vacation rentals in Skokie?

    Skokie has family friendly vacation rentals, particularly in residential neighborhoods and near local parks. Many options feature spacious layouts and easy access to playgrounds or nature centers.

  • What are the best places to stay in Skokie?

    Skokie has vacation rentals near Downtown, around parks, and in residential neighborhoods, giving easy access to shopping and locally rooted restaurants. Look for options with amenities suited to your group, and consider stays close to public transit for added convenience.

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 $57 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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