We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Apartment in Park Ridge

4.79 out of 5 average rating, 321 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

9–16 Jan

$260 NZD per night

Guest favourite

Apartment in Evanston

4.95 out of 5 average rating, 115 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 20 min walk for trains to city, 5 min drive to lake. Wifi

7–14 Sep

$323 NZD per night

Guest favourite

Guesthouse in Evanston

4.98 out of 5 average rating, 202 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

5–12 Mar

$298 NZD per night

Guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

13–20 Sep

$204 NZD per night

Guest favourite

Guest suite in Evanston

4.97 out of 5 average rating, 213 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 guest suite w/private kitchen, 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!

29 Nov – 6 Dec

$213 NZD per night

Guest favourite

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

During this time, we are taking extra precautionary measures to ensure our guests safety. Cute and private micro studio in phenomenal downtown Wilmette location. Steps from all local restaurants, shopping, and the Metra station. Walkable to Gillson Beach and the Linden CTA stop. Enter through the front gate to an open & shared yard with private, single access to the unit. Pets OK with additional pet fee (some breed / weight restrictions).

21–28 Jun

$252 NZD per night

Guest favourite

Apartment in Evanston

4.95 out of 5 average rating, 210 reviews

Crisp and Clean 2BD Getaway Near Downtown Evanston

My top floor, 2 bedroom home sits in a quiet cul-de-sac, about a mile 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.

17–24 Nov

$341 NZD per night

Guest favourite

Guest suite in Evanston

4.83 out of 5 average rating, 326 reviews

Huge, cozy one bedroom semi-basement apartment

1000 SF Close both to Chicago area and the lake and the suburbs. It has a side separate entrance from the main house. One bedroom with one queen bed. A pull out couch too. A fully equipped kitchen. One full bathroom with a shower , no tub. A cozy living room with TV. This propery has surveillance cameras . Strict rules will be applied to violation of maximum capacity of 4 people. The place is not rented for parties !

13–20 Mar

$186 NZD per night

Guest favourite

Apartment in Skokie

4.91 out of 5 average rating, 531 reviews

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

7–14 Apr

$252 NZD per night

Guest favourite

Guest suite in Chicago

4.94 out of 5 average rating, 177 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

16–23 Sep

$219 NZD per night

Guest favourite

Apartment in Skokie

4.97 out of 5 average rating, 120 reviews

Charming Apt.Fully Equipped Prk.Inc 12 min 2 Lake

Newly renovated, 2-bedroom apartment. New appliances. Relaxing atmosphere. Walking distance to shopping, restaurants, grocery, train station, etc. Nice and quiet neighborhood. Central air & heating, washer & dryer, iron & ironing board, shampoo, conditioner, body wash, hair dryer, coffee maker, toaster, large fridge. All kitchen utensils available for use.

22–29 Aug

$323 NZD per night

Apartment in Evanston

4.83 out of 5 average rating, 215 reviews

Adorable 1BR apartment near Northwestern

Cozy and comfortable one bedroom apartment with full kitchen and updated bath. Recently re-decorated with fresh carpet, paint and new queen bed. Located on the second floor of a single family 2-flat style home in a quiet, residential neighborhood. Ample, free street parking. One additional person can be accommodated with blow-up mattress.

22–29 Sep

$290 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Skokie holiday rentals

Free parking on premises

Air conditioning

Stay near Skokie's top sights

Westfield Old Orchard18 locals recommend

Lincolnwood Town Center12 locals recommend

Illinois Holocaust Museum & Education Center6 locals recommend

Pita Inn10 locals recommend

AMC Village Crossing 189 locals recommend

Maggiano's Little Italy3 locals recommend

Other great holiday rentals in Skokie

Guest favourite

Guest suite in Skokie

4.86 out of 5 average rating, 148 reviews

Adorable studio style unit - Self check in ⚡️

31 Jul – 7 Aug

$373 NZD per night

Guest favourite

Guest suite in Chicago

5.0 out of 5 average rating, 293 reviews

Private Lincoln Square one bed+bath studio apt.

17–24 Sep

$309 NZD per night

Guest favourite

Apartment in Chicago

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

9–16 Jul

$251 NZD per night

Guest favourite

Guest suite in Chicago

4.96 out of 5 average rating, 102 reviews

1BR Historic Rogers Park/West Ridge unit- Sleeps 4

22–29 Mar

$245 NZD per night

Guest favourite

Guest suite in Chicago

4.93 out of 5 average rating, 352 reviews

Peaceful Portage Park Apartment

15–22 Jan

$244 NZD per night

Apartment in Chicago

4.88 out of 5 average rating, 104 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

23–30 Jan

$253 NZD per night

Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

23–30 Sep

$309 NZD per night

Guest favourite

Home in Skokie

4.87 out of 5 average rating, 86 reviews

A+amazing beauty, entire 2 BR Skokie historic stay

23–30 Mar

$197 NZD per night

Quick stats about holiday rentals in Skokie

Total rentals
130 properties
Wi-Fi availability
120 properties include access to Wi-Fi
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
6.2K reviews

Destinations to explore