Bridgeport Vacations from $333

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

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

    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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $485, price is now $333 per person
$333
per person
Dec 11 - Dec 14
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Comfy bed and great view. Nice staff.

Reviewed on Oct 2, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Price was $620, price is now $489 per person
$489
per person
Dec 14 - Dec 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
the staff was exceptional and our dinner was very good

Reviewed on Sep 17, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $771, price is now $642 per person
$642
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
This hotel was convenient for us because it is located close to family. The room was clean, and the front desk staff were very helpful. During our stay, on a Friday night, tnere was a lot of loud noise from a nearby room. We called the front desk, and they handled the matter. The free breakfast was good.

Reviewed on Oct 2, 2025

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
Price was $573, price is now $488 per person
$488
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9/10 Wonderful! (1,007 reviews)
2 night stay, great amenities, able to work remotely. Breakfast options were good (different every day) and jacuzzi and pool was nice ✨

Reviewed on Oct 1, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $573, price is now $507 per person
$507
per person
Dec 14 - Dec 16
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,005 reviews)
Yes it was very nice

Reviewed on Oct 3, 2025

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

Where to stay in Bridgeport

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

West End - West Side

While West End - West Side might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Seaside Beach and Seaside Park.

Find hotels in West End - West Side

Discover the most popular places to visit in Bridgeport

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
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

Hartford HealthCare Amphitheater

Catch an event at Hartford HealthCare Amphitheater during your trip to Bridgeport. Stroll along the beautiful beaches or attend a sporting event in the area.

Hartford HealthCare Amphitheater

Bridgeport Hotel Deals

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
40 Beechmont Ave, Bridgeport, CT
$916 nightly
The price is $1,054 total per night from Oct 9 to Oct 10
$1,054 total
Oct 9 - Oct 10
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Nov 2 to Nov 3
$127 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,677 reviews)
"Clean room and friendly and helpful staff"

Reviewed on Oct 4, 2025

Amsterdam Hotel
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $141 total per night from Oct 19 to Oct 20
$141 total
Oct 19 - Oct 20
Total with taxes and fees
8.6/10 Excellent! (1,323 reviews)
"Beautiful hotel"

Reviewed on Oct 2, 2025

Norwalk Inn & Conference Center
See all 1,297 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.

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 $333 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

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.