Bridgeport Vacations from $465

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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.
Quality Inn

Quality Inn

2.5 out of 5
Price was $523, price is now $465 per person
$465
per person
Jan 21 - Jan 26
found 7 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Evansville (EVV)
7.6/10 Good! (117 reviews)
The staff was very friendly and greeted us kindly will definitely stay again

Reviewed on Dec 14, 2025

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was $670, price is now $584 per person
$584
per person
Jan 21 - Jan 26
found 7 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Evansville (EVV)
8.6/10 Excellent! (508 reviews)
Staff was excellent.we like staying here when we come to town for family .

Reviewed on Nov 8, 2025

Baymont by Wyndham Evansville North/Haubstadt

Baymont by Wyndham Evansville North/Haubstadt

2.5 out of 5
Price was $518, price is now $470 per person
$470
per person
Jan 21 - Jan 26
found 7 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Evansville (EVV)
7.6/10 Good! (1,000 reviews)
The furniture in the hotel room was dirty. The staff was nice.

Reviewed on Dec 14, 2025

Comfort Inn Henderson - Evansville South

Comfort Inn Henderson - Evansville South

2.5 out of 5
Price was $630, price is now $575 per person
$575
per person
Jan 21 - Jan 26
found 7 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Evansville (EVV)
8.2/10 Very Good! (311 reviews)
Didn't like that the Coffee maker is in the Bathroom

Reviewed on Sep 7, 2025

Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was $581, price is now $532 per person
$532
per person
Jan 21 - Jan 26
found 7 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Evansville (EVV)
8/10 Very Good! (280 reviews)
Needs proper upgrades to bathtub area. They have renovated some areas of motel like solar panels, one EV plug.Spent money on kiost to check in and out with,instead of spending more on upgrades to rooms.

Reviewed on Nov 24, 2025

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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 refundable
$86 nightly
The price is $96 total per night from Jan 10 to Jan 11
$96 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
7.8/10 Good! (338 reviews)
Breakfast was ok. Hot food was hot and fresh. Breakfast area nice and clean. Staff friendly Room was clean. Common areas and elevator could use deep clean.

Reviewed on Dec 7, 2025

Holiday Inn Express Princeton by IHG
Country View Inn & Suites

Country View Inn & Suites

2.5 out of 5
100 Abraham Lincoln Robinson IL
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $138 total per night from Jan 2 to Jan 3
$138 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
9.2/10 Wonderful! (275 reviews)
Very good room. Clean. Service very good. Personnel knowledgeable and professional

Reviewed on Nov 29, 2025

Country View Inn & Suites
Hampton Inn Princeton

Hampton Inn Princeton

2.5 out of 5
107 S Richland Creek Dr Princeton IN
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Jan 3 to Jan 4
$105 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
9/10 Wonderful! (508 reviews)
The front desk staff was friendly and super efficient. Room was clean and it was one of the best night of sleep that I have had in a hotel room, 9:30 pm until 4:30 am. No noise at all. Excellent

Reviewed on Dec 12, 2025

Hampton Inn Princeton
See all 68 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 $465 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.