Near North Side holiday lettings

We found 1,136 holiday rentals — enter your dates for availability

Discover a selection of 529 apartments, 29 flats and other holiday rentals in Near North Side that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Near North Side

Showing deals for:5 Dec - 12 Dec

Image gallery for Luxury House in the heart of Old Town with Parking

Loft Living Space with Deep, Comfortable Sofa, Smart Flat Screen TV & Fireplace
10 out of 10 rating
Exceptional
(50 reviews)

Luxury House in the heart of Old Town with Parking

Chicago, IL

11% off
Price is £10,263
for 7 nights, 1 home
£1,466 nightly
Includes taxes & fees
Luxury House in the heart of Old Town with Parking

Find spaces that suit your style

  • 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, 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 rental in Near North Side?
In Near North Side, apartments are the most popular type of holiday rental, with about 42 available throughout this vibrant neighbourhood. These apartments typically feature modern amenities, including fully equipped kitchens, comfortable living areas, and often access to communal facilities such as fitness centres or rooftop terraces, allowing guests to enjoy views of the city skyline. For those seeking a more spacious option, there are around 17 holiday houses that cater to families or larger groups. These homes usually come with multiple bedrooms, private gardens, and outdoor seating areas, providing a great setting for relaxation after a day of exploring local attractions like the Magnificent Mile and Lincoln Park.
Are there any beach house rentals in Near North Side?
In Near North Side, Illinois, there are several beach house rentals available, offering a unique stay by the waterfront. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them great for families or groups. Many rentals also include outdoor spaces such as balconies or patios, allowing guests to enjoy views of Lake Michigan and the bustling city life. The area is in close proximity to popular attractions like the Magnificent Mile, Navy Pier, and Lincoln Park, providing plenty of options for dining, shopping, and entertainment.
How much does it cost to rent a holiday home in Near North Side?
Prices for holiday rentals in Near North Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Near North Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Near North Side holiday house rentals?
You can find great discounts on house rentals in Near North Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Near North Side holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Near North Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Near North Side?
A long-stay holiday rental in Near North Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Near North Side?
In the Near North Side of Chicago, there are numerous remote work-friendly holiday rentals available, with around 47 options to choose from. This vibrant area is known for its lively atmosphere, featuring a mix of historic architecture and modern amenities. Many properties come equipped with essential remote work amenities such as Wi-Fi, dedicated desk spaces, and comfortable desk chairs, making it easy for travellers to stay productive during their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Near North Side holiday rental?
Book your Near North Side holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Near North Side?
In Near North Side, visitors can explore a variety of attractions that showcase the vibrant culture and history of Chicago. One of the most prominent sites is the Magnificent Mile, a bustling stretch of Michigan Avenue filled with high-end shops, restaurants, and iconic landmarks. Nearby, the historic Water Tower and the Chicago Riverwalk offer picturesque settings for leisurely strolls.

For art enthusiasts, the Museum of Contemporary Art is located within this neighbourhood, featuring an impressive collection of modern art and engaging exhibitions. The area is also home to the famed Chicago Avenue, where the iconic Chicago Theatre can be found, often hosting a range of performances and events.
Can I change or cancel my Near North Side home rental booking on Vrbo?
To find Near North Side holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Near North Side holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Holiday Rentals ideas

Costa del Sol Holiday Rentals
Standard Link for Costa del Sol
Albany Park Holiday Rentals
Standard Link for Albany Park
Wicker Park Holiday Rentals
Standard Link for Wicker Park
Davenport Holiday Rentals
Standard Link for Davenport
Torquay Holiday Rentals
Standard Link for Torquay
Spain Holiday Rentals
Standard Link for Spain
Logan Square Holiday Rentals
Standard Link for Logan Square
Hyde Park Holiday Rentals
Standard Link for Hyde Park
Little Italy Holiday Rentals
Standard Link for Little Italy
Lakeview Holiday Rentals
Standard Link for Lakeview
Magnificent Mile Holiday Rentals
Standard Link for Magnificent Mile
Andersonville Holiday Rentals
Standard Link for Andersonville
Lincoln Park Holiday Rentals
Standard Link for Lincoln Park
Keswick Holiday Rentals
Standard Link for Keswick
Albufeira Holiday Rentals
Standard Link for Albufeira
Ravenswood Holiday Rentals
Standard Link for Ravenswood
Isle of Anglesey Holiday Rentals
Standard Link for Isle of Anglesey
The Loop Holiday Rentals
Standard Link for The Loop
Glenrothes Holiday Rentals
Standard Link for Glenrothes
Sydney Holiday Rentals
Standard Link for Sydney
Charmouth Holiday Rentals
Standard Link for Charmouth
Rush and Division Holiday Rentals
Standard Link for Rush and Division
North Devon District Holiday Rentals
Standard Link for North Devon District
Downtown Chicago Holiday Rentals
Standard Link for Downtown Chicago
West Loop Holiday Rentals
Standard Link for West Loop
The Galena Territory Holiday Rentals
Standard Link for The Galena Territory
Fulton Market Holiday Rentals
Standard Link for Fulton Market

People also search for

Lapland Cabin Rentals
Standard Link for Lapland
West Sussex Cottages
Standard Link for West Sussex
Downtown Chicago Apartments
Standard Link for Downtown Chicago