Bridgeport Holiday Rentals
About Casai's Private Villas and Holiday Rentals in Bridgeport
Discover more than 1443 vacation rentals available in Bridgeport. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Bridgeport.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Bridgeport, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Bridgeport. On average, places to stay near Bridgeport offer 783.27 ft², with nightly prices averaging CA $497.
With Casai, finding and comparing holiday rentals in Bridgeport is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Bridgeport
| Type | Count |
|---|---|
| Holiday Apartments | 1059 |
| Vacation Homes | 138 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Bridgeport
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Bridgeport.
Weather in Bridgeport, IL
View the weather forecast for Bridgeport before booking your Bridgeport Vacation Rentals to confirm your best time to go.
Other Places to Stay in Bridgeport, IL
Frequently Asked Questions About Bridgeport?
What are the top holiday rentals in Bridgeport?
With numerous options available in Bridgeport, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
- 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 holiday rentals have private pools in Bridgeport?
Discover a selection of holiday rentals with private pools near Bridgeport with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Jeffjack Heated Pool Penthouse in Chicago's West Loop
- S Loop Studio w Pool Gym Spa nr Grant Park CHI-739
- South Loop 1br w gym game room nr top schools CHI-988
- Hampton Inn & Suites Chicago Medical District Uic
Which holiday homes in Bridgeport are best for families?
If you're searching for a family-friendly holiday home in Bridgeport, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Bridgeport:
- Spacious unit in historic gem
- Cozy 3BR City Living in South Loop Near McCormick Place, Soldier Field & Lakefront
- SpringHill Suites by Marriott Chicago Chinatown
How many Casai.ca holiday rentals are available in Bridgeport?
As of 2026, Casai boasts over 1443 properties listed in the Bridgeport area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Bridgeport.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Lower West Side Vacation Rentals in Chicago, Illinois | 55 |
| Armour Square Vacation Rentals in Chicago, Illinois | 1372 |
| McKinley Park Vacation Rentals in Chicago, Illinois | 797 |
