Bridgeport Vacations from $214

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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.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $262, price is now $214 per person
$214
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Myrtle Beach (MYR) to New Haven (HVN)
8.6/10 Excellent! (1,184 reviews)
Clean room, hot water took some time to come on in the shower

Reviewed on Dec 23, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $423, price is now $307 per person
$307
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Myrtle Beach (MYR) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Everything was amazing

Reviewed on Dec 14, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,772, price is now $1,313 per person
$1,313
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
No reviews
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 $421, price is now $321 per person
$321
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Myrtle Beach (MYR) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Breakfast was huge, but expensive

Reviewed on Dec 15, 2025

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Save 100% on your flight
Price was $540, price is now $418 per person
$418
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Myrtle Beach (MYR) to New Haven (HVN)
No reviews
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Where to stay in Bridgeport

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

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

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from Dec 30 to Dec 31
$113 total
Dec 30 - Dec 31
Total with taxes and fees
9/10 Wonderful! (1,939 reviews)
Great hotel. Really nice reception person. Fast process. Nice room. I recommend fully with 5 stars + .

Reviewed on Dec 19, 2025

New Haven Hotel
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Dec 29 to Dec 30
$124 total
Dec 29 - Dec 30
Total with taxes and fees
8.2/10 Very Good! (1,029 reviews)
Great hidden gem

Reviewed on Dec 16, 2025

EVEN Hotel Norwalk by IHG
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
$135 nightly
The price is $155 total per night from Jan 4 to Jan 5
$155 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
Overall it was a good place to stay

Reviewed on Dec 17, 2025

DoubleTree by Hilton Stamford
See all 1,321 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

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Frequently asked questions

How much does a Bridgeport vacation package cost?
Offering great value package deals from $214 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.