The Loop Cottage Rentals
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $253/Night
For 7 Nights US $1,771
398.26 ft²
2 Guests
12 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $278/Night
For 7 Nights US $1,943
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $131/Night
For 7 Nights US $919
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $546/Night
For 7 Nights US $3,825
1435.19 ft²
32 Guests
13 Bedrooms
12 Bathrooms
Apartment
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,582/Night
For 7 Nights US $11,076
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $632/Night
For 7 Nights US $4,426
3003.13 ft²
16 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
Apartment
- Parking
- Air Conditioner
- Internet
US $1,407/Night
For 7 Nights US $9,848
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $485/Night
For 7 Nights US $3,398
2249.66 ft²
13 Guests
5 Bedrooms
4 Bathrooms
House
- View
- Parking
- Air Conditioner
US $734/Night
For 7 Nights US $5,141
8 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $1,215/Night
For 7 Nights US $8,508
1496.18 ft²
12 Guests
3 Bedrooms
2 Bathrooms
House
- Balcony/Terrace
- View
- Parking
US $275/Night
For 7 Nights US $1,925
7 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $1,233/Night
For 7 Nights US $8,630
Why Choose Rent By Owner for your The Loop 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.
Weekly Weather Forecast for The Loop
How to Book Your The Loop 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
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in The Loop
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 The Loop, IL
Chicago
333 West Wacker Drive
Civic Opera House
Printers Row
Cadillac Palace Theatre
Chicago City Hall
Willis Tower
Lakeshore East
Near East Side
Chicago
Central Chicago
Downtown Chicago
The Loop Cottage Rentals Frequently Asked Questions
1. What are the top Cottages in The Loop?
There are a lot of options in The Loop. If you plan on staying in the The Loop area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in The Loop:
- 55th Floor Penthouse with Award-Winning Views
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- Smart Home in Logan Square by the 606 Trail
- Splendid Corner 3BR in the Loop | City Views
- Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
- 5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 14.
- 50th Floor Mag Mile Views, Balcony, Pool, Gym
- Downtown 3bd #7 near Park+Museums
- Downtown 3bd Penthouse| Lake Mich VIEWS +gym
- Delightful Room w/Whimsical Decor & Modern Amenities Near Magnificent Mile
2. How many Cottages are available in The Loop?
Currently, the total number of properties listed by RBO in 2026 is over 1200 in the The Loop area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in The Loop.
More Rentals You May Like Near The Loop
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Pool
- Parking
- Air Conditioner
US $1,516/Night
For 7 Nights US $10,612
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $438/Night
For 7 Nights US $3,069
735 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $422/Night
For 7 Nights US $2,953
6458 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $205/Night
For 7 Nights US $1,432
2600 ft²
8 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $1,191/Night
For 7 Nights US $8,338
1109 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $826/Night
For 7 Nights US $5,783
700 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $272/Night
For 7 Nights US $1,903
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $922/Night
For 7 Nights US $6,454
1500 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Kitchen
- Air Conditioner
- Internet
US $960/Night
For 7 Nights US $6,720
1098 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $859/Night
For 7 Nights US $6,013
667 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $582/Night
For 7 Nights US $4,076
667 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $574/Night
For 7 Nights US $4,019
