Skokie Holiday Rentals

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Holiday Rentals in Skokie

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (429)
"Nice place very nice front desk"
The price is NZ$375
per night
3 Jul - 4 Jul
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (95)
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is NZ$158
per night
30 Jun - 1 Jul
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (312)
"Pretty nice but the outlet and few other items not functioning "
The price is NZ$364
per night
2 Jul - 3 Jul
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (251)
"Had some difficulty finding a USB charging port. It was located under the kitchen counter-top."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (214)
"The staff here is amazing and so helpful. Loved my stay here. "
The price is NZ$480
per night
16 Jun - 17 Jun
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (132)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$302
per night
7 Jul - 8 Jul
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (78)
"I like the hotel, I did not realize there was no cleaning services or fresh towels. After 4 days the room needed some freshing and clean wash rags and towels. There was a washing machine but doing laundry on vacation is not for me."
The price is NZ$462
per night
8 Jul - 9 Jul
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (34)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (188)
"Very nice property "
The price is NZ$156
per night
10 Jun - 11 Jun
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (68)
"Room was great! Spacious, clean and perfect for a night or longer stay. View was also very nice!"
The price is NZ$690
per night
12 Jun - 13 Jun
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (107)
"Loved it "
The price is NZ$368
per night
7 Jul - 8 Jul
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (162)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$378
per night
2 Jul - 3 Jul
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"The place was nice and clean but missing some basic items such as floor mats and decent pans, otherwise our stay was good. It was near all the places we need to go"
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is NZ$347
per night
10 Jun - 11 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (40)
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (200)
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.2 out of 10, Very good, (15)
"I like that was contactless and easy to access. "
The price is NZ$451
per night
1 Jul - 2 Jul
Sonder The Opal
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (8)
"My friends and I stsyed with Alma for a Girl's Weekend. Our stay was comfortable and Alma was there for everything we needed. She was very accommodating. The listing was the perfect place to come to after a long day of exploring Chicago."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Skokie you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6873)
"Situated on the ‘Miracle Mile’, Chicago’s Congress Plaza is perfectly situated as a central point for exploring the city’s many attractions. The hotel is a perfect mix of old world charm with modern amenities and the staff are friendly and responsive to their guest’s requests. I would recommend it to anyone looking to spend some time in this eclectic city. "
The price is NZ$286
per night
18 Jun - 19 Jun
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, (2378)
"Very good location "
The price is NZ$354
per night
16 Jun - 17 Jun
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2964)
"Excellent property "
The price is NZ$312
per night
7 Jul - 8 Jul
River Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Skokie holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Skokie. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Skokie. Seeing all the best attractions is bound to make you fall in love with Skokie. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Skokie short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Skokie?

Yes, there are holiday rentals in Skokie close to Adagio Teas, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Skokie. Make sure you allow time to enjoy the gardens during your holiday.

What are some of the best holiday rentals that Skokie has to offer?

Luxury Home Away From Your Home: This holiday home rental outside of Skokie has air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Skokie?

Expedia has 10 holiday rentals for your stay in Skokie.

What can I see and do in Skokie?

Adagio Teas and Schaefer's Wines and Liquors are a couple of the family-friendly sights, whereas cultural attractions include Skokie Theatre and North Shore Center for the Performing Arts. While in the area, you can also visit popular places such as Wrigley Field and Navy Pier.

What are holiday rentals like in Skokie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Skokie. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for small groups.

Recent reviews of Skokie properties
Expedia verified reviews