Compare Cottages, Resorts, & Rentals in Bridgeport, Chicago, Illinois, USA
About Bridgeport Vacation Rentals
There are over 1435 amazing vacation rentals available in Bridgeport. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Bridgeport.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Bridgeport, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Bridgeport. The average size of places to stay near Bridgeport is approximately 781.52 ft², with prices averaging US $350 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Bridgeport. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Bridgeport, IL
Frequently Asked Questions About Bridgeport?
What are the top cottages, summer homes, and lake houses 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
- Cozy Pilsen Depa
- MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- The Suite Spot Eclectic Modern Central Sleeps 6
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Family Friendly 2-Bedroom w/Kitchen & Laundry
- Luxury Modern home minutes from Downtown Chicago
- Penthouse, Lux stay near Downtown, McComick & Lake
How many rentals, hotels, or resorts are available in Bridgeport?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 1435 properties listed by Vacation Cottage in the Bridgeport area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Bridgeport.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Lower West Side Rental Cottages and Private Getaways in Chicago, Illinois | 55 |
| Armour Square Rental Cottages and Private Getaways in Chicago, Illinois | 1372 |
| McKinley Park Rental Cottages and Private Getaways in Chicago, Illinois | 797 |
