Bridgeport Vacations from $539

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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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $616, price is now $539 per person
$539
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
Price was $730, price is now $553 per person
$553
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
8.4/10 Very Good! (1,005 reviews)
Staff is very friendly. Rooms and common areas are in need of updating, carpets in particular. Linens and bath are clean but room smelled a bit musty. On site tavern is fun. Lauren and Simon are great bartenders 😁. Breakfast is a bit pricey for a small buffet breakfast.

Reviewed on Nov 8, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,184, price is now $1,003 per person
$1,003
per person
Dec 30 - Jan 2
found 20 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $848, price is now $746 per person
$746
per person
Dec 30 - Jan 2
found 20 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.6/10 Excellent! (1,105 reviews)
Perfect place to stay when visiting Yale! Just adjacent to the heart of campus and you feel so very well supported!!

Reviewed on Nov 8, 2026

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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
A rocky shoreline at sunset with the sun setting over the water.

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

Stay near popular Bridgeport attractions

A city street lined with parked cars and tall buildings.
Photo by Mark Ferg
Open Photo by Mark Ferg

Bridgeport Downtown South Historic District

8.0/10 (5 reviews)
Wander through Bridgeport's architectural time capsule, where Victorian facades tell stories of the city's evolution. The district rewards explorers with hidden galleries and eateries among historic buildings.
See properties

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
$130 nightly
The price is $150 total per night from Nov 27 to Nov 28
$150 total
Nov 27 - Nov 28
Total with taxes and fees
New Haven Hotel
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
700 East Main Street Stamford CT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Nov 22 to Nov 23
$183 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (1,264 reviews)
"The property is conveniently located and he to travel from and to."

Reviewed on Nov 8, 2026

The Stamford Hotel
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
2701 Summer St Stamford CT
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $213 total per night from Dec 10 to Dec 11
$213 total
Dec 10 - Dec 11
Total with taxes and fees
7.8/10 Good! (1,009 reviews)
"Everything was excellent!! Except the breakfast they don’t provide breakfast you have to pay. And about the 100$ I don’t know why, but they do 100 $ and don’t know if they gave it back!!! But the hotel wooow very beyond perfect!!!😍"

Reviewed on Nov 8, 2026

The Armon Stamford Hotel & Conference
See all 1,394 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

Things to do in and around Bridgeport

Bridgeport, Connecticut, is perfect for outdoor family vacations and city-themed getaways. Visitors can enjoy exciting activities such as the Bridgeport Adventure, explore educational attractions, and take advantage of the arena entertainment facilities. The city's recreational areas offer a great escape for day trips, making it a popular destination for memorable experiences and adventures.

Shopping

For shopping in Bridgeport, visit the Westfield Connecticut Post Mall, offering a vibrant atmosphere with entertainment and dining options just 9 miles away. If you're up for a drive, check out Caldor Shopping Center, 12 miles away, featuring a mix of businesses and family-friendly vibes.

Recreation

Experience live events at Hartford HealthCare Amphitheater, where the vibrant atmosphere energizes your spirit. For relaxation, unwind at Seaside Park, where scenic views and tranquil paths invite you to rejuvenate. Tee off at Fairchild Wheeler Golf Course, offering an outdoor escape just a few miles from the city.

Adventure

The Adventure Park at Discovery Museum in Bridgeport offers exhilarating zipline and ropes course experiences amidst nature. For family fun, the Lighthouse Point Carousel, located 16 miles away, provides delightful rides with scenic views. Blue Jay Orchards, 17 miles from Bridgeport, invites you to enjoy apple picking and farm activities.

Nightlife

Bridgeport's nightlife offers vibrant spots like The Acoustic, where live music creates a lively vibe, and the downtown bars that serve craft cocktails and local brews. For a more relaxed evening, enjoy a cozy atmosphere at The Bijou Theatre, catching a film or performance.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Bridgeport

Bridgeport, Connecticut, offers a delightful mix of outdoor activities and family-friendly attractions, making it perfect for a city-themed vacation. Visitors can enjoy beautiful beaches, explore local parks, and engage with the vibrant culture. Whether you're looking to relax by the shore or immerse yourself in urban experiences, Bridgeport's top attractions cater to all interests and ensure a memorable getaway.

  • Bridgeport Downtown South Historic District: Immerse yourself in the rich history and charming architecture of this historic village. With its vibrant cultural atmosphere, you can explore unique shops, galleries, and local eateries that reflect the area's heritage.
  • Total Mortgage Arena: Enjoy a family-friendly entertainment experience at this lively arena. Hosting concerts, sports events, and shows, it offers a dynamic atmosphere perfect for a fun outing with friends or family, making lasting memories.
  • Jennings Beach: Relax and unwind at this beautiful beach located 4 miles from Bridgeport. With soft sands and inviting waters, it's an ideal spot for sunbathing, swimming, and enjoying beach activities, perfect for a day of leisure.

Best time to go to Bridgeport

The best time to visit Bridgeport can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Bridgeport falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Bridgeport falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.8°F (-0.1°C)Light RainMostly SunnySlightly LowSlightly Low
February32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
March39.0°F (3.9°C)Light RainMostly SunnyAverageSlightly Low
April48.9°F (9.4°C)Light RainMostly SunnyAverageAverage
May58.8°F (14.9°C)Light RainMostly SunnyAverageSlightly High
June67.6°F (19.8°C)Light RainMostly SunnySlightly HighSlightly High
July74.8°F (23.8°C)Light RainMostly SunnySlightly HighSlightly High
August73.9°F (23.3°C)Light RainMostly SunnyAverageAverage
September67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
October57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
November46.2°F (7.9°C)Light RainMostly SunnySlightly LowAverage
December38.3°F (3.5°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Bridgeport

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Bridgeport.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

What's included in a Bridgeport vacation package?
A Bridgeport vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Most hotels here offer airport shuttle service, making transfers convenient from airports like Bradley International Airport (BDL). Additionally, about half of hotels include free breakfast, providing a good start to your day. Nearly all properties also offer free WiFi and parking.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Bridgeport vacation package?
When you bundle, you can save up to 30%*. To save money on a Bridgeport package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Bridgeport?
A Bridgeport vacation can feature a mix of entertainment, outdoor activities, and family-friendly attractions:

Browse and book things to do in Bridgeport on Expedia.
Do you need to rent a car in Bridgeport, or is public transport enough?
For a Bridgeport vacation, a rental car offers the most flexibility for exploring the area, especially since it's an outdoor and nature destination outside the city. While some central areas like the Bridgeport Downtown South Historic District are easily walkable, about a 10-minute walk from central Bridgeport, many attractions are spread out. For instance, Fairfield Beach is about 7 miles away, and Silver Sands State Park is about 14 miles from central Bridgeport.

Travelers booking Bridgeport vacation packages with flights often arrive at major hubs such as Newark Liberty Intl. Airport (EWR) or John F. Kennedy Intl. Airport (JFK). Having a car allows for convenient day trips to these wider regional sights.
Can I change or cancel my Bridgeport vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Bridgeport vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Bridgeport vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Bridgeport vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Bridgeport?
To find last-minute vacation packages to Bridgeport, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Bridgeport vacation packages?
Free cancellation on a Bridgeport vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Bridgeport vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Bridgeport getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Bridgeport vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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.