Lakeview holiday rentals

We found 345 holiday rentals — enter your dates for availability

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August 2025

September 2025

Find the perfect place for you stay in Lakeview by choosing from 29 houses, 39 flats and other holiday rentals. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Lakeview

Showing deals for:14 Nov - 21 Nov

Exceptional

(12 reviews)

Luxurious, custom built single family home near Wrigley

Chicago, IL

7% off

AU$2,105 per night

includes taxes & fees

Exceptional

(40 reviews)

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Chicago, IL

13% off

AU$2,043 per night

includes taxes & fees

Centrally located in the North Center neighborhood of Chicago's northside.

Exceptional

(22 reviews)

The Irving Park Hideaway – Prime Location w/ Patio & Parking!

Chicago, IL

7% off

AU$471 per night

includes taxes & fees

Exceptional

(51 reviews)

PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!

Chicago, IL

7% off

AU$2,390 per night

includes taxes & fees

Bright and sunny owner's unit penthouse loft with private outdoor deck

Exceptional

(98 reviews)

Unique Chicago Penthouse Loft - Amazing Deal & Location

Chicago, IL

11% off

AU$637 per night

includes taxes & fees

Exceptional

(143 reviews)

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

Chicago, IL

7% off

AU$514 per night

includes taxes & fees

Spacious living room features a cozy couch, ceiling fans and natural light.

Exceptional

(9 reviews)

St.Bens, Jacuzzi, EV Parking! 4 beds, Walk to Wrigley Field & Brown Line!

Chicago, IL

7% off

AU$809 per night

includes taxes & fees

Exceptional

(46 reviews)

"Holy Cow"! 4bed 4bath Duplex Penthouse w/ 3,000 sqft Private Roof-Deck!

Chicago, IL

15% off

AU$2,246 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Lakeview

Wrigley Field

Find the best place to stay - Lakeview

Wrigleyville Suites

Sleeps 22 · 9 bedrooms

The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals - Lakeview

Premier Host

50th Birthday Celebration

We had a wonderful time and Dustin was an excellent host! He was gracious, responsive and communication was excellent! Such fun memories! Thanks for everything!

Cindy J H.

Stayed Sept 2023

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Lakeview?

Apartments are the most popular kind of holiday home in Lakeview, according to our data. Even if you have something else in mind, Stayz has properties in a variety of shapes and sizes. Look through our options to find your perfect pad.

How much does it cost to rent a holiday home in Lakeview?

A number of things determine how much you pay for a holiday home in Lakeview, such as the season, length of stay and type of property. However, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Lakeview?

The average price for a holiday home near the beach in Lakeview depends on when you'll be there and the size and type of property you're looking for. Find prices easily on Stayz by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities essential to you, like a pool, air conditioning and WiFi.

Are there pet-friendly holiday homes in Lakeview?

With 140 properties that welcome four-legged guests, your furry little friend can also come along on your Lakeview holiday. Use our filter tool to search our pet-friendly holiday homes and find your pawfect holiday home on Stayz.

Can I rent a house with a pool in Lakeview?

Check the "pool" box in our filter tool and select from 13 houses with private pools in Lakeview on Stayz. Morning dip, sunset soak or midnight swim? Leisure activities are up to you when your Stayz holiday home has a swimming pool.

What are popular home amenities in Lakeview?

Some of the most popular home amenities people look for in Lakeview include a nearby waterfront, a fireplace and tennis. Whether you're travelling with family, friends or even pets, Stayz holiday homes include the best amenities for making epic memories with the people you cherish the most.

Are there large group holiday homes in Lakeview?

You can choose from 15 properties in Lakeview that can host a group of 10 or more guests. Whether you're planning a trip with extended family or an event like an anniversary, there's enough space to get your group together under the same roof.

Are there holiday homes in Lakeview that welcome kids?

With 140 family-friendly holiday properties available in Lakeview, now is an awesome time to introduce your children to the wonders of travel. Simply click on our "Properties good for families" filter box to look for stays that come with amenities perfect for travelling families, such as living rooms, patios, bunk beds and entertainment areas.

What are the top attractions for families in Lakeview?

Keeping the kids happy during your Lakeview holiday is a breeze with these leading family-friendly attractions:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

Are there one-bedroom holiday homes in Lakeview?

Take your pick from 41 one-bedroom homes in Lakeview. Whether you'd like a townhouse or a condo, our one-bedroom properties are just right if you don't require a lot of space. One of the perks of having your own digs? You won't ever need to share your adventure with strangers.

Can I find two-bedroom holiday homes in Lakeview?

Gather your loved ones and enjoy peace, privacy and comfort in one of the 44 two-bedroom holiday properties Lakeview has to offer.

Are there holiday homes with WiFi in Lakeview?

Lakeview has 30 holiday homes with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Stayz homes make it a breeze to get online.

How can I find holiday homes with air conditioning in Lakeview?

You'll find 133 Stayz holiday homes with air conditioning in Lakeview offering that cooling breeze and extra bit of comfort. Just enter your preferred travel dates and then take advantage of our filters to search for properties with air conditioning.

How old do you have to be to rent a holiday home in Lakeview?

The minimum required age is normally 16, 18 or 21. It can vary from one property to another on Stayz, so look at the rules of your preferred Lakeview stay before booking your escape.

How long can I rent a holiday home in Lakeview for?

The amount of time you can stay in a Lakeview holiday home for is up to the property. Simply tap in your dates of travel to view available options that offer long-term stays. They come with the things you need to make your extended trip more enjoyable such as air conditioning and kitchens. Some holiday homes might also offer weekly or monthly discounts, so you can stick around for longer for less.