1338+ Vacation Rentals & Holiday Homes in Bridgeport |
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Bridgeport Accommodations - Hotels & Rentals

About Bridgeport Vacation Rentals

Discover More than 1338 Incredible Getaway Rentals Available in Bridgeport. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Bridgeport.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Bridgeport, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Bridgeport. The Average Size of Places to Stay Near Bridgeport is 805.45 ft², with Prices Averaging US $358 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Bridgeport. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Bridgeport

Type Count
Holiday Apartments 971
Vacation Homes 123
Villas 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Bridgeport

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Bridgeport with Online Reservations.

Weather in Bridgeport, IL

View the weather forecast for Bridgeport before booking your Bridgeport Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Palmisano Park 1,984 Properties
Theatre on the Lake 1,291 Properties
Stephen A. Douglas Tomb and Memorial 1,095 Properties
Zhou B Art Center 1,070 Properties
Bridgeport Art Center 1,055 Properties
Bubbly Creek 1,044 Properties

Frequently Asked Questions About Bridgeport?

What are the top hotels, lake houses & vacation rentals in Bridgeport?

We provide an array of great vacation destinations in Bridgeport. If you are looking to stay in or around the Bridgeport area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Bridgeport:

How many Hotels & Vacation Rentals have private pools in Bridgeport?

We have 15 Hotels & Vacation Rentals featuring a private pool in and near Bridgeport. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Bridgeport is best for families?

Searching for a family-friendly getaway in Bridgeport? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Bridgeport?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 1338 in the Bridgeport area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Bridgeport.

Nearby Neighborhood (3) 
Neighborhood Property Count
Lower West Side Vacation Rentals in Chicago, Illinois 51
Armour Square Vacation Rentals in Chicago, Illinois 1338
McKinley Park Vacation Rentals in Chicago, Illinois 739

People Also Ask

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