Downtown Bridgeport Vacation Packages for 2025

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Top Hotel Deals

Holiday Inn Bridgeport-Trumbull-Fairfield, an IHG Hotel

Holiday Inn Bridgeport-Trumbull-Fairfield, an IHG Hotel

4 out of 5
1070 Main St, Bridgeport, CT
0.3 km from Downtown Bridgeport
Stay at this 4-star business-friendly hotel in Bridgeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Hartford HealthCare ...
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
19.93 km from Downtown Bridgeport
Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
26.12 km from Downtown Bridgeport
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
19.34 km from Downtown Bridgeport
Stay at this 4-star hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular ...
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
20.85 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
5.26 km from Downtown Bridgeport
Stay at this 3-star beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
The Watershed

The Watershed

3.5 out of 5
353 Main Ave, Norwalk, CT
20.07 km from Downtown Bridgeport
Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
14.8 km from Downtown Bridgeport
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr, New Haven, CT
26.18 km from Downtown Bridgeport
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
12.57 km from Downtown Bridgeport
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Blake Hotel

The Blake Hotel

4 out of 5
9 High Street, New Haven, CT
26.05 km from Downtown Bridgeport
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
25.56 km from Downtown Bridgeport
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
26.34 km from Downtown Bridgeport
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

4 out of 5
500 Sargent Drive, New Haven, CT
26.35 km from Downtown Bridgeport
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Quality Inn

Quality Inn

2 out of 5
7 Kimberly Ave, West Haven, CT
24.05 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions New Haven Harbor and Long Wharf ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, Sep 5 - Thu, Sep 11
MCO
Orlando Intl.
HPN
Westchester County
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Westchester County, returning Thu, Sep 11, priced at $139 found 4 days ago
JetBlue Airways
Wed, Sep 3 - Mon, Sep 8
MCO
Orlando Intl.
HPN
Westchester County
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Orlando Intl. to Westchester County, returning Mon, Sep 8, priced at $157 found 6 days ago
American Airlines
Fri, Sep 5 - Thu, Sep 11
MCO
Orlando Intl.
HPN
Westchester County
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to Westchester County, returning Thu, Sep 11, priced at $187 found 4 days ago
Delta
Tue, Aug 5 - Wed, Aug 13
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Wed, Aug 13, priced at $197 found 1 hour ago
Frontier Airlines
Tue, Jul 22 - Wed, Jul 30
CLT
Charlotte-Douglas Intl.
ISP
MacArthur
$264 Roundtrip, found 6 days ago
$264
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jul 22 from Charlotte-Douglas Intl. to MacArthur, returning Wed, Jul 30, priced at $264 found 6 days ago