Bridgeport Vacations from $407

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Bridgeport Vacation

Prepare to experience Bridgeport in your own style with a custom Bridgeport vacation package! Discovering the best parts of this fascinating city is easy with a base in a neighborhood such as Black Rock Historic District, which is good for history, among many other things. Fairfield University, Total Mortgage Arena and Sacred Heart University are just some of the sights you'll want to check out during your trip to Bridgeport. Your perfect Bridgeport vacation is only clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Bridgeport vacation packages

Price found within the past 48 hours. Click for updated prices.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $609, price is now $407 per person
$407
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
9/10 Wonderful! (1,874 reviews)
The room was amazing the staff was great very helpful especially the desk attendant. Would stay here again.

Reviewed on Nov 28, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,729, price is now $1,072 per person
$1,072
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
No reviews
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $592, price is now $409 per person
$409
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
Absolutely loved this place. The lobby and room were great. I would stay at this location and with this chain again.

Reviewed on Nov 28, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $674, price is now $485 per person
$485
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Nice throwback hotel. Room was spotless, much old school charm. Check in was a little bumpy, otherwise a good stay.

Reviewed on Nov 17, 2025

The Blake Hotel

The Blake Hotel

4 out of 5
Downtown New Haven
Price was $684, price is now $504 per person
$504
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to New Haven (HVN)
9.4/10 Exceptional! (1,000 reviews)
Great ambiance, cozy decoration. Clean and comfortable rooms, love the kitchen, the bathroom on the room. Very spacious. Very friendly staff. Valet parking very convenient.

Reviewed on Nov 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Bridgeport
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
Default Image

Black Rock Historic District

Travelers enjoy Black Rock Historic District for its beaches and restaurants. Consider checking out Longfellow Park while you're in the area.

Find hotels in Black Rock Historic District

Discover the most popular places to visit in Bridgeport

Bridgeport Downtown South Historic District

Bridgeport Downtown South Historic District

You can learn about the history of Bridgeport with a stop at Bridgeport Downtown South Historic District. Experience the live music and theater scene in this walkable area.

Bridgeport Downtown South Historic District
Gathering of the vibes 2014

Seaside Park

If a restful vacation is part of your travel plans, Seaside Park might be the perfect place to seek out during your trip to Bridgeport. Amble around the area's parks or experience its live music.

Seaside Park

Total Mortgage Arena

Catch an event at Total Mortgage Arena during your trip to Bridgeport. Amble around this family-friendly area's beautiful beaches or attend a sporting event.

Total Mortgage Arena

Bridgeport Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Dec 25 to Dec 26
$85 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (1,894 reviews)
Great location to restaurants and bars, room was clean, easy access to parking for fee

Reviewed on Nov 24, 2025

New Haven Hotel
DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl Stamford CT
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $178 total per night from Dec 21 to Dec 22
$178 total
Dec 21 - Dec 22
Total with taxes and fees
7.4/10 Good! (1,014 reviews)
From the moment I checked in to the moment I left, the staff was kind and welcoming. They were helpful and everyone was incredibly friendly to the 4 preteen boys who were with me. Clean lobby, clean room, clean pool. I will definitely go back!

Reviewed on Nov 24, 2025

DoubleTree by Hilton Stamford
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Dec 20 to Dec 21
$119 total
Dec 20 - Dec 21
Total with taxes and fees
8.4/10 Very Good! (1,725 reviews)
Rooms clean. Halls smell of either cigarette smoke or marijuana. Everything freshly painted it must be in the carpets. My room was clean and odor free.

Reviewed on Nov 24, 2025

Amsterdam Hotel
See all 1,306 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
Closest Airport
MacArthur Airport (ISP)
Population
147,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Jennings Beach, Compo Beach and Beardsley Zoo

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Bridgeport vacation package cost?
Offering great value package deals from $407 on Expedia, you'll be pleasantly surprised at how much a vacation to Bridgeport costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Bridgeport?
You can typically find lower rates and better availability in December, January and February. Check out our cheap Bridgeport vacation packages and you could get some great off-season deals.
How many days is enough for Bridgeport?
Bridgeport vacations come in all shapes and sizes, but to really get a feel for this place, we'd say 2 days is a good ballpark. With this timeframe, you can visit headline attractions like Downtown Cabaret Theatre and Discovery Museum along with underrated spots. Don't forget to explore cool areas such as East Bridgeport Historic District and Brooklawn - St. Vincent either. If you plan wisely, you may even be able to take a day trip from Bridgeport too.
Is it worth booking a vacation package to Bridgeport?
Well known for its history and home to leading attractions like Hartford HealthCare Amphitheater, a Bridgeport vacation is sure to leave an impression. Another top sight to visit? Don't miss Beardsley Zoo.
How to find the best Bridgeport package deals?
Begin your search for a Bridgeport package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Bridgeport package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Bridgeport adventure underway.
Is it cheaper to book a Bridgeport vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights separately. Better still, you can personalize your Bridgeport getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Bridgeport?
If you're planning an impromptu Bridgeport getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Bridgeport?

  1. Pick your dates: The things you plan to do in Bridgeport and your preferred season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Bridgeport.
  3. Organize your Bridgeport getaway with our trip planning tool: Look for and book accommodations and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Bridgeport together.
  4. Work out your trip length: Think about how long you'd like to spend exploring Bridgeport. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Combine your airfare and accommodations: After you've settled on your dates and duration, book the right Bridgeport vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to see and do. Check out some of the exciting things to do in Bridgeport and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Bridgeport vacation packages?
Set off on your dream trip to Bridgeport with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snag great deals before they sell out.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.