Bridgeport Cottage Rentals & Holiday Homes

Frequently Asked Questions About Bridgeport Rental Cottages

What are the top rated Cottage Rentals in Bridgeport?

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

• Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
• 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
• 1F Chicago's Little italy Graystone nearDowntown
• 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
• Cozy Pilsen Depa
• MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
• The Suite Spot Eclectic Modern Central Sleeps 6
• Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
• 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
• Family Friendly 2-Bedroom w/Kitchen & Laundry

How much does it cost to rent a cottage in Bridgeport?

The average cost for a cottage rental in Bridgeport is $153 per night. Vacation Cottage has a wide list of great cottages near Bridgeport that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Bridgeport that allow pets?

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

• Urban Cottage
• Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.
• Lux Apts with Lake Views and Top Amenities
• Mccormick Place Guest House
• Zen 5 Bedroom Family Escape

See all pet-friendly vacation rentals in Bridgeport on Vacation Cottage

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

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

Are there quality cottages in Bridgeport that have indoor swimming pools?

As of 2025, the data from Vacation Cottage shows that there are Over 1 private swimming pools or cottages with indoor pools in the Bridgeport area along with other great amenities.

Do any cottages in Bridgeport have hot tubs?

About 1 cottages in Bridgeport boast of premium hot tubs. Some of the popular places to stay with hot tubs include:

• Bridgeport rentals with hot tub

Are there luxury cottages in Bridgeport?

Yes, there are luxury cottages in Bridgeport. Find more luxury, lakefront, winter, & last-minute cottage rentals near Bridgeport.