Skokie holiday homes
We found 1,919 holiday rentals — enter your dates for availability
Discover a selection of 16 homes and other holiday rentals in Skokie that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Skokie
Showing deals for:18 Jul - 25 Jul
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

1010 out of 10 rating
Exceptional
(20 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
8% off
Price is NZ$83,516
NZ$83,516
NZ$11,931 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment

9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,446
NZ$11,446
NZ$1,635 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
12% off
Price is NZ$15,341
NZ$15,341
NZ$2,192 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,164
NZ$5,164
NZ$738 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes

1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
7% off
Price is NZ$14,549
NZ$14,549
NZ$2,078 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking

1010 out of 10 rating
Exceptional
(12 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$16,395
NZ$16,395
NZ$2,342 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

9.89.8 out of 10 rating
Exceptional
(31 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,721
NZ$7,721
NZ$1,103 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,570
NZ$4,570
NZ$653 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago

9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,707
NZ$4,707
NZ$672 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago

9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,289
NZ$4,289
NZ$613 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views

9.49.4 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,826
NZ$7,826
NZ$1,118 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,289
NZ$4,289
NZ$613 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

9.49.4 out of 10 rating
Exceptional
(25 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$8,414
NZ$8,414
NZ$1,202 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago

1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,164
NZ$5,164
NZ$738 per night
includes taxes & fees
Image gallery for SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

9.89.8 out of 10 rating
Exceptional
(80 reviews)
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Chicago, IL
8% off
Price is NZ$7,492
NZ$7,492
NZ$1,070 per night
includes taxes & fees
Image gallery for The Executive Residence -Luxury 5 Br 4.5 Ba- 0.8 acre- 5400 sqft- Lake Community

9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Executive Residence -Luxury 5 Br 4.5 Ba- 0.8 acre- 5400 sqft- Lake Community
Prospect Heights, IL
8% off
Price is NZ$10,003
NZ$10,003
NZ$1,429 per night
includes taxes & fees
Image gallery for Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

1010 out of 10 rating
Exceptional
(8 reviews)
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Chicago, IL
12% off
Price is NZ$7,503
NZ$7,503
NZ$1,072 per night
includes taxes & fees
Image gallery for Chic 4-Bedroom Haven: Designer's Dream Home

1010 out of 10 rating
Exceptional
(5 reviews)
Chic 4-Bedroom Haven: Designer's Dream Home
Chicago, Illinois
12% off
Price is NZ$11,103
NZ$11,103
NZ$1,586 per night
includes taxes & fees
Image gallery for Across from Wrigley Field: Patio, Free Parking&Iconic Rooftop Views on Waveland

1010 out of 10 rating
Exceptional
(25 reviews)
Across from Wrigley Field: Patio, Free Parking&Iconic Rooftop Views on Waveland
Chicago, IL
8% off
Price is NZ$22,754
NZ$22,754
NZ$3,251 per night
includes taxes & fees
Image gallery for NEW! 10-min to Downtown | LCP Collection

9.69.6 out of 10 rating
Exceptional
(7 reviews)
NEW! 10-min to Downtown | LCP Collection
Oak Park, IL
9% off
Price is NZ$9,272
NZ$9,272
NZ$1,325 per night
includes taxes & fees
Image gallery for A quiet stay while you are away

9.89.8 out of 10 rating
Exceptional
(32 reviews)
A quiet stay while you are away
Oak Park, IL
9% off
Price is NZ$4,647
NZ$4,647
NZ$664 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!

9.69.6 out of 10 rating
Exceptional
(11 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago, IL
8% off
Price is NZ$14,849
NZ$14,849
NZ$2,121 per night
includes taxes & fees
Image gallery for Mid Century Elegance in Evanston Vintage Apartment.

1010 out of 10 rating
Exceptional
(14 reviews)
Mid Century Elegance in Evanston Vintage Apartment.
Evanston, IL
12% off
Price is NZ$3,954
NZ$3,954
NZ$565 per night
includes taxes & fees
Image gallery for Convenient Location Near Loyola/Northwestern

1010 out of 10 rating
Exceptional
(19 reviews)
Convenient Location Near Loyola/Northwestern
Chicago, IL
8% off
Price is NZ$7,153
NZ$7,153
NZ$1,022 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Skokie
Skokie 9 bed 4 bedrooms house
Sleeps 15 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Sleeps 6 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Cozy 2 bedroom house/w garage in Skokie
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Free Parking, Private Terrace Up to 10%off on 30day stay
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Skokie?
According to our research, condos are the most sought-after type of property in Skokie. But of course, everyone’s idea of the perfect stay isn’t going to be the same. Bookabach has holiday homes with every size, shape and budget in mind, so you’re bound to find your perfect match.
How much does it cost to rent a holiday home in Skokie?
Length of stay, property type and time of year are some of the conditions that can affect the price of a holiday home. Simply click on your travel dates to find your dream escape. From cosy chalets to expansive villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Skokie?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside escape. Put in your Skokie travel dates to see all your options on Bookabach. Looking for basics like WiFi, or perks like a private pool? Use the filters to pick the amenities and features you want.
Are there pet-friendly holiday homes in Skokie?
Pack a suitcase and a bone for your pooch because Skokie has nine stays that roll out the welcome mat to doggie guests. Let your four-legged buddy have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Skokie?
Dig out your swimsuit and inflatable unicorn, because there are two houses with a private pool in Skokie. Kick back at one of these terrific holiday homes and enjoy a pool day every day. Simply enter your dates into Bookabach, then use the “pool” filter to find the ideal place for a splashing good time!
What are popular home amenities in Skokie?
When it comes to home amenities that people are on the lookout for in Skokie, a barbecue grill, a firepit and a swimming pool rank the highest. With Bookabach holiday homes, you’ll find options to match your style and taste, whether you’re going on a holiday with friends, relatives or even pets.
Are there large group holiday homes in Skokie?
Yes, there are two properties in Skokie that can sleep five or more guests. From family get-togethers to events like birthday parties, these stays have ample room to hang out with your favourite people.
Are there holiday homes in Skokie that welcome kids?
Skokie has nine family-friendly holiday homes. And discovering a stay that welcomes children is a cinch with our “Properties good for families” filter. In addition to having the whole place to yourselves, you’ll also enjoy access to perks and conveniences like extra bedrooms, kitchens and yards.
What are the top attractions for families in Skokie?
There are lots of fabulous things to see and do with the family in Skokie, such as:
- Parkway Bank Park Entertainment District
- Montrose Beach
- Kohl Childrens Museum
Are there one-bedroom holiday homes in Skokie?
Yes, Skokie has two one-bedroom homes available. Often positioned in prime spots because of their compact size, a one-bedroom property is ideal if you’re getting away with your partner or a pal. And with comforts such as kitchens and more privacy than a standard hotel, you’ll be able to kick back while discovering this terrific destination.
Can I find two-bedroom holiday homes in Skokie?
Skokie has five two-bedroom holiday properties to select from. Find a holiday home with all the comfort and space you’re looking for at a price that’s hard to resist on Bookabach.
Are there holiday homes with WiFi in Skokie?
Pick from five holiday homes with WiFi in Skokie. If you want to disconnect from the world during your trip, but still need to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Skokie?
Skokie has nine holiday homes where you’ll be able to relax and recharge in air-conditioned comfort. To find a property on Bookabach with this perk, enter your desired travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Skokie?
The minimum age can differ across properties on Bookabach, so be sure to check the rules of the holiday home in Skokie you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Skokie for?
The amount of time you can book a Skokie holiday home for depends on the property. Simply enter your travel dates to browse options offering extended stays. They include all you need to make your extended trip more convenient and enjoyable, such as kitchens and laundries. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.