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Bailey Island Cottage Rentals & Holiday Homes

Find the best cottages in Bailey Island - We found 77 exact matches

About Bailey Island Cottage Rentals on Chicago\92s Best Vacation Rentals

Searching for cottages to rent near Bailey Island? Chicago\92s Best Vacation Rentals features more than 77 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Bailey Island have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Chicago\92s Best Vacation Rentals’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Bailey Island.

Are you planning to travel to the lakeside, beach, or mountain area? Chicago\92s Best Vacation Rentals’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Chicago\92s Best Vacation Rentals boasts of 77 holiday cottages and places to stay in Bailey Island. The site provides unique Airbnb, VRBO, Chicago\92s Best Vacation Rentals-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Frequently Asked Questions About Bailey Island Cottage Rentals

What are the top rated Cottage Rentals in Bailey Island?

There are a lot of options in Bailey Island. If you plan on staying in the Bailey Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Bailey Island:

How much does it cost to rent a cottage in Bailey Island?

The average cost for a cottage rental in Bailey Island is $401 per night. Chicagosbestvacationrentals has a wide list of great cottages near Bailey Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Bailey Island that allow pets?

Yes, here are the top cottage rentals in Bailey Island that allow you to bring your pet:

See all pet-friendly vacation rentals in Bailey Island on Chicagosbestvacationrentals

Do you have any rental cottages in Bailey Island that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Bailey Island to find one that works for you.

Are there quality cottages in Bailey Island that have indoor swimming pools?

As of 2026, the data from Chicagosbestvacationrentals shows that there are Over 77 private swimming pools or cottages with indoor pools in the Bailey Island area along with other great amenities.