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Holiday houses in Skokie

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Quick stats about holiday rentals in Skokie

  • Total holiday rentals

    Explore 130 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 5,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 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!

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 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, 313 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 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, 120 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
Townhouse in Skokie
5 out of 5 average rating, 13 reviews

Family Retreat Destination, House of Joy Skokie

Welcome to HOUSE OF JOY SKOKIE, your Kosher Ready destination within the Skokie Aruv! Beautifully remodeled, hosts 12, including 3 bedrooms, 1.5 baths + recreation room + stunning kitchen open to living room. Walk to kosher eateries, walk to synagogues: Israeli + Skokie Chabad, Or Torah, Chovavei Tzion and Skokie Valley. Enjoy Starbucks, walk to train + buses. Private front deck with grill and parking spot. Welcome to your peaceful, comfortable Simcha (Happiness) Spot, House of Joy Skokie, LLC.

Top Guest favourite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 497 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

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, 92 reviews

Cozy, sun drenched, spacious, perfect location!

This is a 3 bedroom and 2 bath home with split basement located in a quiet safe suburb of Skokie with ample parking. It is within walking distance to Skokie downtown and 3 minutes from i-94 highway which will take you directly to downtown Chicago in 30 minutes. Alternatively 5 minutes from the Metra or CTA station which will also take you downtown Chicago. 20 minutes from Northwestern campus. This house is all yours with plenty of space to prepare meals, work, and get some needed rest.

Guest favourite
The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.
Guesthouse in Evanston
4.94 out of 5 average rating, 140 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

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, 101 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
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
4.98 out of 5 average rating, 294 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 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, 245 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 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, 61 reviews

"Hope of Evanston" 2BDR/2BTH, Gym+Pool

Enjoy a stylish experience at this centrally-located place in downtown Evanston, IL. Urban-Luxe experience at the Hope of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 1 roll-out bed in closet, welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

Guest favourite
Home in Skokie
4.83 out of 5 average rating, 6 reviews

Luxury fenced in modern ranch

Escape to the stunning remodeled, exquisite upscale mid-century modern luxury ranch near downtown Skokie three blocks from the subway, Skokie waterpark and Evanston golf club-and by staying at the stunning property, you are in the heart of Skokie at the edge of downtown with easy access to almost everything! Relax and unwind in my fenced in yard or perhaps use the pizza maker to help make a pizza with the kids! For worship needs, I am 2 blocks away from Church and Temple.

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, 221 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 holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Skokie's top sights

Westfield Old Orchard

33 locals recommend

Skokie Northshore Sculpture Park

20 locals recommend

Illinois Holocaust Museum & Education Center

15 locals recommend

The Spice House

13 locals recommend

Emily Oaks Nature Center

12 locals recommend

Leaning Tower Of Niles

10 locals recommend

Other great holiday rentals in Skokie

Top Guest favourite
Apartment in Evanston
4.97 out of 5 average rating, 38 reviews

Private entrance to bed, bath, lounge and kitchen

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
4.83 out of 5 average rating, 120 reviews

Quiet and welcoming house.

Apartment in Skokie
4.75 out of 5 average rating, 4 reviews

Skokie Serenity - 3 queen beds

Guest favourite
Apartment in Skokie
5 out of 5 average rating, 13 reviews

30-Night Min Stay 3BR-2Car Driveway 2nd Flr (Top)

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
4.88 out of 5 average rating, 112 reviews

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

Guest favourite
Apartment in Evanston
4.89 out of 5 average rating, 36 reviews

Evanston Garden Guest House

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
4.73 out of 5 average rating, 51 reviews

Skokie 1BR Stay Near Parks, Dining & Transit

Top Guest favourite
Shipping container in Evanston
5 out of 5 average rating, 11 reviews

Container home. Walk to NWU and Central Street.

When is the best time to visit Skokie?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$193 AUD$196 AUD$213 AUD$216 AUD$226 AUD$237 AUD$209 AUD$213 AUD$198 AUD$191 AUD$191 AUD$193 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 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.

  • 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.

Destinations to explore