Chicago Cottage Rentals By Owner

Chicago Cottage Rentals

Private Cozy Cottage House in Lincoln Park w/Porch

10.0

Exceptional

(1 Review)

Private Cozy Cottage House in Lincoln Park w/Porch

4 Guests 1 Bedroom 1 Bathroom

Family Friendly Cottage

Fireplace/Heating
Balcony/Terrace
Kitchen

AU $220/Night For 7 Nights AU $1,544

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New

Corporate Housing for Travel Nurses and Interns Located Near O'Hare & Hospitals

1100 ft² 4 Guests 1 Bedroom 1 Bathroom

Family Friendly Cottage

Fireplace/Heating
Balcony/Terrace
Kitchen

AU $155/Night For 7 Nights AU $1,083

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New

Classic Workers Cottage in Vibrant Bucktown Chicago.

7 Guests 3 Bedrooms 2 Bathrooms

Cottage

Internet
Child Friendly
Laundry

AU $330/Night For 7 Nights AU $2,311

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Stay near family or close to downtown, this cottage in Beverly has it all!

10.0

Exceptional

(6 Reviews)

Stay near family or close to downtown, this cottage in Beverly has it all!

6 Guests 3 Bedrooms 2 Bathrooms

Family Friendly Cottage

Fireplace/Heating
Pet Friendly
Kitchen

AU $300/Night For 7 Nights AU $2,099

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5.0

Average

(2 Reviews)

Urban Cottage

4 Guests 1 Bedroom 1 Bathroom

Family Friendly Cottage

Kitchen
Air Conditioner
Child Friendly

AU $215/Night For 7 Nights AU $1,503

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A 3-bedroom, 2-bathroom residence that provides ample space and comfort.

New Property

10.0

Exceptional

(1 Review)

A 3-bedroom, 2-bathroom residence that provides ample space and comfort.

1500 ft² 6 Guests 3 Bedrooms 2 Bathrooms

Family Friendly Apartment

Fireplace/Heating
Balcony/Terrace
Kitchen

AU $369/Night For 7 Nights AU $2,583

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Cozy Modern 1BR Apt, 10-min Walk to Wrigley Field - Stratford 1E 3E rep

10.0

Exceptional

(14 Reviews)

Cozy Modern 1BR Apt, 10-min Walk to Wrigley Field - Stratford 1E 3E rep

699.65 ft² 2 Guests 1 Bedroom 1 Bathroom

Apartment

Internet
Child Friendly

AU $359/Night For 7 Nights AU $2,515

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Highly Rated

10.0

Exceptional

(505 Reviews)

The Sono Chicago

1 Bedroom 1 Bathroom

Couples Retreat Bed & Breakfast

Fireplace/Heating
Balcony/Terrace
Parking

AU $196/Night For 7 Nights AU $1,372

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Cozy 2-bedroom apartment in Pilsen Chicago

New Property

10.0

Exceptional

(1 Review)

Cozy 2-bedroom apartment in Pilsen Chicago

6 Guests 2 Bedrooms 1 Bathroom

Apartment

Fireplace/Heating
Air Conditioner
Internet

AU $308/Night For 7 Nights AU $2,157

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10.0

Exceptional

(12 Reviews)

Uptown Gem

452.08 ft² 4 Guests 1 Bedroom 1 Bathroom

Apartment

Private Pool
Oceanfront
Fireplace/Heating

AU $164/Night For 7 Nights AU $1,149

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3BR near U Chicago and Obama Center, Easy Parking

New Property

8.0

Excellent

(1 Review)

3BR near U Chicago and Obama Center, Easy Parking

6 Guests 3 Bedrooms 1 Bathroom

Apartment

Fireplace/Heating
Air Conditioner
Internet

AU $719/Night For 7 Nights AU $5,032

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Wicker Park 1-BR Walk to Train & Grocery Easy Downtown Access

10.0

Exceptional

(8 Reviews)

Wicker Park 1-BR Walk to Train & Grocery Easy Downtown Access

495.14 ft² 2 Guests 1 Bedroom 1 Bathroom

Apartment

Pet Friendly
Parking
Air Conditioner

AU $262/Night For 7 Nights AU $1,837

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More Top-Rated Cottage Rentals in Chicago Area

Why Choose Rent By Owner for your Chicago Cottage Rentals?

What makes our Cottage Rentals special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

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How to Book Your Chicago Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Chicago

More Top-Rated Cottage Rentals in Chicago Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Chicago, IL

Chicago

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Frequently Asked Questions About Chicago Rental Cottages

1. What are the top Cottages in Chicago?

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Chicago:

2. How many Cottages are available in Chicago?

Currently, the total number of properties listed by RBO in 2026 is over 5 in the Chicago area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Chicago. 