Bridgeport Vacations from $586

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Your Bridgeport Vacation

Enjoy unforgettable adventures when you reserve a vacation package to Bridgeport. Whether you're a foodie, history enthusiast or just a traveler who loves to experience new places, there's something for everyone in this vibrant city. Your trip to Bridgeport has to include a little sightseeing. Red Hills State Park is a great place to kick things off. Whoever you're escaping with and whether your budget is big or small, your ultimate Bridgeport vacation is just clicks away with Expedia.

The Latest Bridgeport vacation packages

Price found within the past 48 hours. Click for updated prices.
New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was $644, price is now $586 per person
$586
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Evansville (EVV)
9/10 Wonderful! (491 reviews)
Very nice facility. Clean, comfortable, great restaurant on site, and very walkable to downtown.

Reviewed on Feb 16, 2026

Holiday Inn Express Evansville by IHG

Holiday Inn Express Evansville by IHG

2.5 out of 5
Price was $753, price is now $691 per person
$691
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Evansville (EVV)
9.4/10 Exceptional! (347 reviews)
Nice clean hotel with a good breakfast

Reviewed on Feb 8, 2026

Holiday Inn Express Princeton by IHG

Holiday Inn Express Princeton by IHG

2.5 out of 5
Price was $645, price is now $593 per person
$593
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Evansville (EVV)
8/10 Very Good! (335 reviews)
Just a pleasant stay. We had everything we needed.

Reviewed on Jan 12, 2026

Holiday Inn Express & Suites Evansville North by IHG

Holiday Inn Express & Suites Evansville North by IHG

2.5 out of 5
Price was $712, price is now $657 per person
$657
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Evansville (EVV)
8.6/10 Excellent! (576 reviews)
Pretty clean, sheets didn’t fit bed. Broken nightstand, various digital outlets didn’t work. Cracked tile in shower. Clerk couldn’t provide a receipt demonstrating the incidental fee had been refunded to me.

Reviewed on Jan 29, 2026

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Bridgeport Hotel Deals

Holiday Inn Express Princeton by IHG

Holiday Inn Express Princeton by IHG

2.5 out of 5
2828 Dixon St Princeton IN
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Mar 1 to Mar 2
$111 total
Mar 1 - Mar 2
Total with taxes and fees
7.8/10 Good! (348 reviews)
Just a pleasant stay. We had everything we needed.

Reviewed on Jan 12, 2026

Holiday Inn Express Princeton by IHG
Country View Inn & Suites

Country View Inn & Suites

2.5 out of 5
100 Abraham Lincoln Robinson IL
9.2/10 Wonderful! (291 reviews)
We came to enjoy the pool and it was wonderful, perfectly heated and lots of tables to hang out at. We had pizza delivered and they were cool with us eating but the pool. Also, I love that they have coffee available in the lobby. I feel relaxed after staying at this hotel.

Reviewed on Feb 1, 2026

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Country View Inn & Suites
Comfort Suites Vincennes

Comfort Suites Vincennes

2.5 out of 5
2555 Hart St Vincennes IN
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $106 total per night from Mar 5 to Mar 6
$106 total
Mar 5 - Mar 6
Total with taxes and fees
8.4/10 Very Good! (550 reviews)
The room was very clean and nice bed pretty quiet and in a good location

Reviewed on Feb 16, 2026

Comfort Suites Vincennes
See all 69 properties in Bridgeport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Bridgeport Vacation Packages

Bridgeport Essential Information

Language
English
Currency
U.S dollars
Population
1,800
Max Temp Winter
40ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Bridgeport vacation package cost?
You can pick up a vacation package to this destination from $586 on Expedia. But how much your vacation to Bridgeport costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Bridgeport?
December, January and February are the best times to look for cheap Bridgeport vacation packages. Opting to travel in quieter periods means you'll typically find lower prices on flights and accommodations.
How many days is enough for Bridgeport?
Usually, a handful of days is enough to check out the top attractions during your Bridgeport vacation. However, if you prefer to have time to chill out or go on day tours, consider extending your trip.
How to find the best Bridgeport package deals?
Use Expedia's filter tool to help you find some terrific Bridgeport package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Bridgeport package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Bridgeport vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights individually. Better still, you can personalize your Bridgeport getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Bridgeport?
If you have your Bridgeport vacation dates confirmed, book early to snap up some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Bridgeport vacation packages?
Your Bridgeport trip is meant to be an escape from your busy life, not a source of money-related stress. So to give you a little more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.