Downtown Bridgeport Vacations from $767
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The Latest Downtown Bridgeport Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartment Near Yale University
Downtown New Haven
$767
per person
Oct 19 - Oct 25
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.
Reviewed on Jun 2, 2026
Water's Edge Resort & Spa
Westbrook Center
$1,108
per person
Nov 21 - Nov 28
found 6 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct .
Reviewed on Sep 12, 2026
Hyatus Luxury Residences City Crossing
The Hill
$1,072
per person
Oct 19 - Oct 25
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Where to stay in Downtown Bridgeport
Find the best Downtown Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Bridgeport
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.
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.
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.
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.
Black Rock Gardens Historic District
Black Rock Gardens Historic District is well-liked for its beaches and waterfront. If you're hoping to see more of the larger area, Seaside Beach and Jennings Beach are some interesting sights nearby to check out.
Downtown Bridgeport Hotel Deals
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Bridgeport CT
$203 nightly
$230 total
Sep 18 - Sep 19
Total with taxes and fees
9.8/10 Exceptional! (17 reviews)
"Everything about this place was as advertised!"
Reviewed on Aug 9, 2026
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Bridgeport CT
$167 nightly
$189 total
Oct 5 - Oct 6
Total with taxes and fees
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$136 nightly
$156 total
Sep 21 - Sep 22
Total with taxes and fees
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.
Stay near popular Downtown Bridgeport attractions
Bridgeport Downtown South Historic District
8.0/10 (5 reviews)
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.
Hartford HealthCare Amphitheater
7.8/10 (7 reviews)
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.
Total Mortgage Arena
8.4/10 (77 reviews)
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.
Barnum Museum
You can spend time exploring the galleries in Barnum Museum in Bridgeport. Stroll along the beautiful beaches or attend a sporting event in this family-friendly area.
Downtown Cabaret Theatre
8.6/10 (4 reviews)
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.
Housatonic Museum of Art
You can spend time browsing the exhibits at Housatonic Museum of Art in Bridgeport. Amble around this family-friendly area's beautiful beaches or attend a sporting event.
Baldwin Plaza Shopping Center
You can browse for the perfect souvenirs at Baldwin Plaza Shopping Center during your stay in Bridgeport. Amble around this family-friendly area's beautiful beaches or attend a sporting event.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.