Title: Bridgeport Vacation Packages & Trips 2026 from CA $598 | Expedia.ca [Bridgeport Travel Guide](https://expedia.ca/Bridgeport.dx525)[Hotels in Bridgeport](https://expedia.ca/Bridgeport-Hotels.d525.Travel-Guide-Hotels)[Vacation Rentals in Bridgeport](https://expedia.ca/Bridgeport-Vacation-Rentals.d525.Travel-Guide-VacationRentals)[Flights to Bridgeport](https://expedia.ca/Cheap-Flights-To-Bridgeport.d525.Travel-Guide-Flights)[Things to do in Bridgeport](https://expedia.ca/Things-To-Do-In-Bridgeport.d525.Travel-Guide-Activities)[Bridgeport Car Rentals](https://expedia.ca/Car-Rentals-In-Bridgeport.d525.Car-Rental-Guide) ![](https://images.trvl-media.com/place/525/df6a44a6-00ef-44dc-9064-a9fe27eefb91.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Bridgeport Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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](https://www.expedia.ca/Fairfield-University-Fairfield.d553248621582621434.Vacation-Attraction), [Total Mortgage Arena](https://www.expedia.ca/Total-Mortgage-Arena-Bridgeport.d6089777.Vacation-Attraction) and [Sacred Heart University](https://www.expedia.ca/Sacred-Heart-University-New-Haven.d553248635056397660.Vacation-Attraction) 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. ## Top Bridgeport Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Mayflower Motel Milford](https://images.trvl-media.com/lodging/2000000/1730000/1721900/1721807/d9e240b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mayflower Motel Milford CA $598 per person Feb 17 - Feb 19 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to New Haven (HVN) 6/10 (549 reviews) We are staying here for a few nights to be close to my family. We drove by Mayflower Motel so many times. We always stayed at a hotel that we were familiar with, big named places Reviewed on Nov 30, 2025 ### Landing Modern 2bd, Gym West New Haven CA $789 per person Feb 23 - Feb 26 found 15 hours ago Roundtrip non-stop flight included Montreal (YUL) to New Haven (HVN) No reviews ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f203cc93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven CA $691 per person Feb 17 - Feb 19 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to New Haven (HVN) 9.2/10 Wonderful! (908 reviews) Great staff, convenient central location, and tasteful retro-collegiate decor in a renovated historic building. Reviewed on Jan 1, 2026 ![James Pharmacy Bed & Breakfast](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### James Pharmacy Bed & Breakfast Old Saybrook Center CA $1,488 per person Apr 3 - Apr 6 found 2 hours ago Roundtrip flight included Halifax (YHZ) to New Haven (HVN) 9.2/10 Wonderful! (20 reviews) Room was pleasant and clean, although small. Bathroom fixtures all new and very clean and functional. Firm bed, which I appreciated. The stairs are steep though there is a firm railing. I didn't realize that we would get a breakfast voucher as opposed to a true B&B experience. The restaurant provided was friendly and the food all looked great but unfortunately didn't have much flavor. The Paperback Cafe nearby had tastier choices. Make sure that you get their email about how to get in because there is no one on site and when we arrived after dark, the front of the building wasn't lit because the entry is in the back. On our first morning, we got a text about our credit card payment not going through. The owner and manager were both responsive but given that they weren't on site, a friendlier tone (i.e., assuming that there might've been a mistake in their information, which there was!) would've been appreciated. It's a lovely place in an excellent location but perhaps slightly expensive given that they are not providing a full B&B experience. Reviewed on Oct 6, 2025 ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 New Haven - Branford, CT CA $605 per person Feb 17 - Feb 19 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to New Haven (HVN) 7/10 Good! (1,001 reviews) The man the helped check me in was super nice. I picked this place because i had an 8am flight & it was very close to the airport. Also the rate was reasonable. The room next door had loud music playing, so i called the front desk. Within 10 - 15 min they turned it down. Reviewed on Dec 2, 2025 ## Where to stay in Bridgeport Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. [Learn more about Bridgeport](https://expedia.ca/Bridgeport.dx525) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Bridgeport 4 out of top 10 points of interest in this area If you're spending some time in Downtown Bridgeport, Bridgeport Downtown South Historic District and Total Mortgage Arena are top sights worth seeing. [Find hotel + flight trips in Downtown Bridgeport](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Bridgeport&DestID=945814454067929088&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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 hotel + flight trips in Black Rock Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Black%20Rock%20Historic%20District&DestID=6347879&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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 hotel + flight trips in West End - West Side](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20End%20-%20West%20Side&DestID=553248635976475205&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### South End 3 out of top 10 points of interest in this area While visiting South End, you might make a stop by sights like Seaside Park and Seaside Beach. [Find hotel + flight trips in South End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20End&DestID=983702209053167616&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### East End While there might not be top attractions in East End, you can explore the larger area and discover places like Total Mortgage Arena and Hartford HealthCare Amphitheater. [Find hotel + flight trips in East End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20End&DestID=553248635976482066&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Things to do in and around Bridgeport Bridgeport, Connecticut, offers a perfect blend of family-friendly activities, outdoor adventures, and urban exploration. Visitors can enjoy various attractions, including recreational areas, educational sites, and shopping districts. For a memorable getaway, explore nearby attractions and friendly locales, or consider day trips to experience the region's charm. Whether you're looking for fun in the sun or cultural experiences, Bridgeport has something for everyone. **Shopping** In Bridgeport, you can explore [Westfield Connecticut Post Mall](https://www.expedia.ca/Westfield-Connecticut-Post-Mall.d6163930.Vacation-Attraction) and [Westport Farmers Market](https://www.expedia.ca/Westport-Farmers-Market.d553248621561886375.Vacation-Attraction), both located 14.5km away, offering vibrant shopping experiences. If you're up for a drive, [Caldor Shopping Center](https://www.expedia.ca/Caldor-Shopping-Center.d553248621557920172.Vacation-Attraction) is 19.3km away, featuring a mix of business and family vibes. **Recreation** [Hartford HealthCare Amphitheater](https://www.expedia.ca/Hartford-HealthCare-Amphitheater.d6178252.Vacation-Attraction) offers a vibrant atmosphere for sports enthusiasts, while [Seaside Park](https://www.expedia.ca/Seaside-Park.d6347889.Vacation-Attraction) invites you to unwind amidst its tranquil landscapes and waterfront views. For a blend of culture and entertainment, visit the [Fairfield Theater Company](https://www.expedia.ca/Fairfield-Theater-Company.d553248621532664592.Vacation-Attraction), only 6.4km away, perfect for a romantic night out or family fun. **Adventure** [The Adventure Park at Discovery Museum](https://www.expedia.ca/The-Adventure-Park-At-Discovery-Museum.d553248621587477416.Vacation-Attraction) offers an exhilarating zipline and ropes course experience, perfect for thrill-seekers. For water sports enthusiasts, [Waterski Connecticut](https://www.expedia.ca/Waterski-Connecticut.d553248621532665672.Vacation-Attraction), located 19.3km away, provides exciting aquatic activities. Don't miss the charming [Lighthouse Point Carousel](https://www.expedia.ca/Lighthouse-Point-Carousel.d553248621532665661.Vacation-Attraction), 25.7km away, ideal for family fun outdoors. **Nightlife** In Bridgeport, Connecticut, explore lively nightlife spots like the Bijou Theatre for live performances, or the downtown area for vibrant bars and clubs. Enjoy the waterfront views at venues like Captain's Cove Seaport, where you can relax with friends while soaking in the lively atmosphere. \*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, is an ideal destination for families and outdoor enthusiasts alike, offering a variety of attractions that cater to different interests. Visitors can enjoy the beautiful beaches, explore local parks, and engage with cultural sites, making it perfect for those seeking a blend of urban and natural experiences. Whether you're looking to relax by the shore or immerse yourself in the city's vibrant atmosphere, Bridgeport has something for everyone. - **[Fairfield University: ](https://www.expedia.ca/Fairfield-University.d553248621582621434.Vacation-Attraction)** Experience the vibrant atmosphere of this modern university, located only 6.4km from Bridgeport. With its stunning campus and city vibes, it's a great place to explore art and culture. - **[Bridgeport Downtown South Historic District: ](https://www.expedia.ca/Bridgeport-Downtown-South-Historic-District.d6348206.Vacation-Attraction)** Immerse yourself in the rich history of Bridgeport as you stroll through this historic district. With its charming architecture and cultural significance, it offers a unique glimpse into the city's past. - **[Total Mortgage Arena: ](https://www.expedia.ca/Total-Mortgage-Arena.d6089777.Vacation-Attraction)** Enjoy family-friendly entertainment at this lively arena located in Bridgeport. From concerts to sporting events, it’s a hub of excitement and fun for all ages. ### Tips to save on your trip to Bridgeport - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Bridgeport. - 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. ## Ready to book your vacation to Bridgeport? Choose your dates ## Bridgeport Hotel Deals ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street New Haven CT Fully refundableReserve now, pay when you stay 9/10 Wonderful! (1,987 reviews) Customer service is top-notch, they are always very accommodating and friendly. We found the hotel to be very clean, the location is extremely convenient to dining shopping and the areas of New Haven. You would want to explore. Parking is extremely convenient and attached to the hotel. There are ... Reviewed on Jan 4, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=525) [](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=525) ![EVEN Hotel Norwalk by IHG](https://images.trvl-media.com/lodging/1000000/10000/2600/2584/4cb7d7eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### EVEN Hotel Norwalk by IHG 426 Main Ave, Route 7 Norwalk CT Fully refundableReserve now, pay when you stay CA $154 CA $178 total Feb 9 - Feb 10 includes taxes & fees 8.2/10 Very Good! (1,046 reviews) I stay here every month I come to CT--safe, great bed, great staff, reliable and not expensive--what more can you want? Reviewed on Jan 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=2584&PinnedHotelID=2584&HadPinnedHotel=true®ionId=525) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Stamford 1 First Stamford Pl Stamford CT Fully refundableReserve now, pay when you stay CA $189 CA $217 total Jan 18 - Jan 19 includes taxes & fees 7.4/10 Good! (1,014 reviews) The customer service was absolutely amazing Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=5292&PinnedHotelID=5292&HadPinnedHotel=true®ionId=525) [See all 1,336 properties in Bridgeport](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F01%2F2026&endDate=12%2F01%2F2026®ionId=525) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Bridgeport #### 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. [](https://expedia.ca/Hartford-HealthCare-Amphitheater-Downtown-Bridgeport.d6178252.Vacation-Attraction) #### Downtown Cabaret Theatre You can enjoy a show at Downtown Cabaret Theatre during your trip to Bridgeport. Amble around this family-friendly area's beautiful beaches or attend a sporting event. 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[Westport Vacations ](https://www.expedia.ca/Westport.d56054.Destination-Travel-Guides) - [Yale University Art Gallery ](https://www.expedia.ca/Yale-University-Art-Gallery-Downtown-New-Haven.d6071487.Vacation-Attraction) - [Yale University ](https://www.expedia.ca/Yale-University-Downtown-New-Haven.d502016.Vacation-Attraction) - [Car rentals in Budget 930 Us 1 ](https://www.expedia.ca/Budget-at-930-Us-1-Vero-Beach-Florida-USA.v8127.Car-Rental-Guide-Location) - [Car rental Stratford ](https://www.expedia.ca/Car-Rentals-In-Stratford.d8127.Car-Rental-Guide) - [Hertz Rental Cars in Gold Coast ](https://www.expedia.ca/Hertz-Car-Rentals-In-Gold-Coast.d6233751-c40.Car-Rental-Guide-Suppliers) - [Gold Coast Vacation Rentals ](https://www.expedia.ca/Gold-Coast-Vacation-Rentals.d6233751.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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