1. USA
  2. Illinois
  3. Chicago
  4. The Loop
  5. Cottage Rentals

The Loop Cottage Rentals & Holiday Homes

Find the best cottages in The Loop - We found 1032 exact matches

About The Loop Cottage Rentals on Online Reservations

For travelers searching for a comfortable and luxurious cottage rental, lake house retreat, or summer home resort in The Loop, Online Reservations has you covered. Consider a cottage rental or holiday home and enjoy more flexibility than a hotel. With over 1032 cottages, lake houses, and summer home retreats in The Loop listed on Online Reservations, we can help you find the perfect place to stay.

Make your next vacation one to remember in a breathtakingly picturesque cottage rental in The Loop featuring top-notch amenities, including swimming pools, fitness centers, Wi-Fi, luxury suites, fully-equipped kitchens, and more. Find incredible outdoor online reservation, lake houses, and summer home retreats at unbeatable prices. Don't wait any longer to start planning your next trip to The Loop and book your accommodation in minutes on our website.

Book for a short-term trip, or find a long-term seasonal cottage rental, lake house or summer home for any of your favorite travel destinations. Compare cottages, lake houses, summer homes and more with Online Reservations. Stay close to nature with Online Reservations.

Show more
Show less

Frequently Asked Questions About The Loop Rental Cottages

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 Cottage Rentals in The Loop:

The average cost for a cottage rental in The Loop is $373 per night. Online Reservations has a wide list of great cottages near The Loop that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in The Loop that allow you to bring your pet:

See all pet-friendly vacation rentals in The Loop on Online Reservations

Most of our listed cottages are suitable for families. Check out the complete list of cottages in The Loop to find one that works for you.
As of 2025, the data from Online Reservations shows that there are Over 1032 private swimming pools or cottages with indoor pools in the The Loop area along with other great amenities.
About 1032 cottages in The Loop boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in The Loop on Online Reservations
Yes, there are luxury cottages in The Loop. Find more luxury, lakefront, winter, & last-minute cottage rentals near The Loop.