Downtown Bridgeport Vacations from $593
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The Latest Downtown Bridgeport Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
$593
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8/10 Very Good! (1,003 reviews)
I have reported this property to the health department. The room was covered in mold. I had an asthma attack within minutes of walking in, and when I went back to the office to address, the concerns, it was met with great attitude until I pulled my phone out and started recording and then they said they would refund me, but they have yet to actually do so.
Reviewed on Sep 16, 2026
Water's Edge Resort & Spa
Westbrook Center
$846
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return.
Reviewed on Sep 15, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$873
per person
Nov 25 - Nov 30
found 13 hours ago
Roundtrip flight included
Raleigh (RDU) 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
Hyatus Luxury Residences City Crossing
The Hill
$1,046
per person
Nov 25 - Nov 30
found 1 hour ago
Roundtrip flight included
Raleigh (RDU) 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.
Brooklawn - St. Vincent
1 out of top 10 points of interest in this area
When in Brooklawn - St. Vincent, you can plan a visit to Bridgeport Downtown South Historic District and Total Mortgage Arena, some noteworthy sights in the nearby area.
Downtown Bridgeport Hotel Deals
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Bridgeport CT
$205 nightly
$232 total
Sep 21 - Sep 22
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Bridgeport CT
$172 nightly
$195 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
$130 nightly
$150 total
Sep 27 - Sep 28
Total with taxes and fees
9.2/10 Wonderful! (2,324 reviews)
"The lobby was nice but the rooms were oddly layout and definitely in need of some updating. The neighborhood was less than amazing."
Reviewed on Sep 16, 2026
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.
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.
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.
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.