11347+ Luxury Vacation Rentals & Cabins in Chicago |
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Chicago Cabin Rentals

About Chicago Vacation Rentals

There are more than 11347 incredible getaway rentals that are available in Chicago. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Chicago.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Chicago, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Chicago. Places to stay near Chicago are 737.58 ft² on average, with prices averaging CA $452 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Chicago. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Chicago

Type Count
Holiday Apartments 5538
Vacation Homes 3102
B&B 59
Cottages 49
Villas 22
Cabin Rentals 15
Others 10
Unique Vacation Rentals 2
Unique Vacation Rentals 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chicago

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chicago with Cabinns.ca.

Weather in Chicago, IL

View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Chicago Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Chicago. Discover Top Attractions For Your Next Outdoor Adventure.


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Cook County 5,364 Properties
Chicago 4,186 Properties
Central Chicago 1,661 Properties
Downtown Chicago 1,523 Properties
West Side 814 Properties
The Loop 701 Properties
North Side 659 Properties
Near North Side 602 Properties
Lake County 562 Properties
DuPage County 451 Properties
Far North Side 383 Properties
South Side 370 Properties

Complexes around Chicago, IL


Wells Apartments St Chicago 132 Properties
Naperville Inn 16 Properties
Town 18 Properties
South Loop Grant Park 29 Properties
Lakeview 20 Properties
Wrigley 31 Properties
Mccormick Place 6 Properties
Kasa River North 12 Properties
Transit Dt 13 Properties
Doubletree 3 Properties
Hilton 6 Properties
Breakfast 17 Properties
Gold Coast Doorman Blocks 9 Properties
Lofts 13 Properties
Courtyard 3 Properties
See More Complexes

Frequently Asked Questions About Chicago?

What are the top cabins, lake houses & summer homes in Chicago?

We provide an array of great vacation destinations in Chicago. If you are looking to stay in or around the Chicago area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chicago:

How many cabin rentals and resorts have private pools in Chicago?

We have 319 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Chicago. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Chicago is best for families?

Searching for a family-friendly cabin in Chicago? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Chicago?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 11347 in the Chicago area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Chicago.

Nearby Neighborhood (16) 
Neighborhood Property Count
Downtown Chicago Rental Cabins and Private Getaways in Chicago, Illinois 1523
The Loop Rental Cabins and Private Getaways in Chicago, Illinois 701
Near North Side Rental Cabins and Private Getaways in Chicago, Illinois 602
South Loop Rental Cabins and Private Getaways in Chicago, Illinois 370
Near South Side Rental Cabins and Private Getaways in Chicago, Illinois 357
River North Rental Cabins and Private Getaways in Chicago, Illinois 317
Lakeview Rental Cabins and Private Getaways in Chicago, Illinois 276
West Loop Rental Cabins and Private Getaways in Chicago, Illinois 220
Lincoln Park Rental Cabins and Private Getaways in Chicago, Illinois 157
Hyde Park Rental Cabins and Private Getaways in Chicago, Illinois 105
Logan Square Rental Cabins and Private Getaways in Chicago, Illinois 87
Edgewater Rental Cabins and Private Getaways in Chicago, Illinois 75
Rogers Park Rental Cabins and Private Getaways in Chicago, Illinois 70
Wrigleyville Rental Cabins and Private Getaways in Chicago, Illinois 54
O'Hare Rental Cabins and Private Getaways in Chicago, Illinois 52
Wicker Park Rental Cabins and Private Getaways in Chicago, Illinois 47

People Also Ask

There are 1823 hotels in Chicago 57 resorts, and 8677 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Chicago