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Vacation rentals in Skokie

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Quick stats about vacation rentals in Skokie

  • Total vacation rentals

    Explore 130 vacation rentals in Skokie

  • Nightly prices starting at

    Skokie vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 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!

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
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.
Apartment in West Rogers Park
4.99 out of 5 average rating, 108 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.

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, 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.

Top guest favorite
Townhouse in Skokie
5 out of 5 average rating, 11 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 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, 114 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.

Top guest favorite
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, 493 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 favorite
The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.
Condo in Evanston
4.96 out of 5 average rating, 144 reviews

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Harmony of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

Top guest favorite
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, 100 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 favorite
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, 293 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 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
4.87 out of 5 average rating, 243 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
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, 220 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.

Top guest favorite
A charming two-story house features a yellow exterior with white trim and a covered porch. Hanging plants adorn the porch, while lush greenery and well-kept landscaping surround the property. A pathway leads to the front steps, framed by stone accents and garden plants.
Apartment in Evanston
4.98 out of 5 average rating, 149 reviews

Charming one bedroom apartment

Downtown Evanston. Cozy quiet area. Lovely studio 1-bedroom apartment. Ideal for a couple or business travelers. One queen size bed. TV & WiFi, microwave, AC & dishwasher. Free off-street parking. Close walk to Northwestern U, Lake Michigan, several supermarkets & many restaurants. Minutes to Metra, Davis & Dempster CTA stations. About 40 minutes to downtown Chicago on CTA Purple Express & less time on Metra. Non-smoking.

Guest favorite
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, 87 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!

Popular amenities for Skokie vacation 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 vacation 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, 119 reviews

Quiet and welcoming house.

Guest favorite
Home in Evanston
5 out of 5 average rating, 13 reviews

4BR Family Home Near Northwestern + Parking

Top guest favorite
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, 47 reviews

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

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

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

Guest favorite
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 favorite
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!

Top guest favorite
The airy living room features a spiral staircase leading to the upper level. A wooden coffee table lies in front of a comfortable sofa. A vibrant vinyl record player sits atop a wooden crate, with bookshelves filled with various titles in the background. Natural light streams through multiple windows.
Guesthouse in Evanston
4.99 out of 5 average rating, 300 reviews

Cottage in a Garden

Superhost
Home in Skokie
4.8 out of 5 average rating, 5 reviews

Luxury fenced in modern ranch

When is the best time to visit Skokie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,450 GYDG$28,868 GYDG$31,379 GYDG$29,705 GYDG$30,333 GYDG$31,169 GYDG$30,751 GYDG$31,379 GYDG$29,078 GYDG$28,032 GYDG$28,032 GYDG$28,450 GYD
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