Bridgeport holiday lettings

We found 43 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Bridgeport that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Bridgeport

Showing deals for:16 Jan - 23 Jan

Image gallery for 1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Living area
9.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago, IL

10% off
Price is £2,688
for 7 nights, 1 home
£384 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

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Frequently asked questions

What is the most popular type of holiday rental in Bridgeport?
In Bridgeport, apartments are a popular choice for holiday rentals, with several available throughout the neighbourhood. These apartments typically offer modern amenities, such as fully equipped kitchens, cosy living areas, and often include in-unit laundry facilities for added convenience. Many are located near local parks and cultural attractions, providing easy access to the vibrant community.
Are there any beach house rentals in Bridgeport?
In Bridgeport, Illinois, there are several beach house rentals available. These properties are typically located near the waterfront, offering easy access to Lake Michigan. Travellers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor patios or decks for enjoying the lake views and fresh air. Many rentals also include modern conveniences like Wi-Fi and laundry facilities, making them ideal for families or groups looking for a comfortable and enjoyable stay.
How much does it cost to rent a holiday home in Bridgeport?
Prices for holiday rentals in Bridgeport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Bridgeport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Bridgeport holiday house rentals?
You can find great discounts on house rentals in Bridgeport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Bridgeport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Bridgeport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Bridgeport?
A long-stay holiday rental in Bridgeport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Bridgeport for a holiday rental?
The best time to visit Bridgeport for a holiday rental is during the peak season, which spans from June to August. This lively period attracts a multitude of travellers eager to experience the local charm and vibrant summer atmosphere. With warm temperatures averaging around 25–30 degrees Celsius, it's an ideal time to explore the area's parks, indulge in outdoor dining, and engage in various recreational activities.

July stands out as the most popular month, drawing visitors who want to soak in the energy of summer festivals and community events. The streets come alive with music and entertainment, offering a fantastic backdrop for those looking to immerse themselves in the local culture.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month presents a unique opportunity to enjoy Bridgeport's attractions without the hustle and bustle of peak season. You can explore local landmarks and enjoy the changing autumn scenery at a more relaxed pace.
Are there any remote work holiday rentals in Bridgeport?
In Bridgeport, Illinois, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated desks, and desk chairs, making them ideal for travellers who need to balance work and leisure. The neighbourhood itself offers a vibrant atmosphere, with parks, local eateries, and cultural attractions nearby, allowing for a pleasant work-life blend. Additionally, the proximity to public transport makes it easy to explore the wider Chicago area during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Bridgeport holiday rental?
Book your Bridgeport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Bridgeport?
In Bridgeport, visitors can enjoy a variety of attractions that reflect the area's rich cultural and historical heritage. The neighbourhood is home to the renowned Chicago White Sox, with Guaranteed Rate Field providing an opportunity to catch a Major League Baseball game during the season. Nearby, the Bridgeport Art Centre showcases local artists and hosts various events, offering a glimpse into the vibrant art scene of the community.
Can I change or cancel my Bridgeport home rental booking on Vrbo?
To find Bridgeport holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Bridgeport holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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