Downtown Bridgeport Vacation Packages for 2026

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Top Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
26.12 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
7.41 km from Downtown Bridgeport
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
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
20.82 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 ...
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
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise 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
Book a stay at this beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Danfords Hotel and Marina

Danfords Hotel and Marina

3.5 out of 5
25 E Broadway Port Jefferson NY
27.46 km from Downtown Bridgeport
Stay at this hotel in Port Jefferson. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
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
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
15.11 km from Downtown Bridgeport
Stay at this hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Watershed

The Watershed

3.5 out of 5
353 Main Ave Norwalk CT
20.07 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
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
Book a stay at this business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue Norwalk CT
19.24 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
Red Carpet Inn

Red Carpet Inn

2 out of 5
1209 E Main St Stamford CT
29.84 km from Downtown Bridgeport
Stay at this hotel in Stamford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Chelsea Piers and Cove Island Park are located ...
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
9.64 km from Downtown Bridgeport
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hartford HealthCare Amphitheater ...
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
19.92 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

3 out of 5
136 Marsh Hill Rd Orange CT
18.26 km from Downtown Bridgeport
Book a stay at this business-friendly hotel in Orange. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
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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
Wed, Aug 26 - Mon, Aug 31
TPA
Tampa Intl.
HPN
Westchester County
$196 Roundtrip, found 9 hours ago
$196
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Tampa Intl. to Westchester County, returning Mon, Aug 31, priced at $196 found 9 hours ago
Delta
Wed, Aug 26 - Mon, Aug 31
TPA
Tampa Intl.
HPN
Westchester County
$228 Roundtrip, found 9 hours ago
$228
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Aug 26 from Tampa Intl. to Westchester County, returning Mon, Aug 31, priced at $228 found 9 hours ago
JetBlue Airways
Tue, Sep 8 - Mon, Sep 14
MCO
Orlando Intl.
HPN
Westchester County
$232 Roundtrip, found 6 days ago
$232
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Sep 8 from Orlando Intl. to Westchester County, returning Mon, Sep 14, priced at $232 found 6 days ago
Avelo Airlines
Wed, Aug 5 - Sat, Aug 8
PBI
Donald J. Trump Intl. Airport
HVN
Tweed - New Haven Regional
$244 Roundtrip, found 19 hours ago
$244
Roundtrip
found 19 hours ago
Select Avelo Airlines flight, departing Wed, Aug 5 from Donald J. Trump Intl. Airport to Tweed - New Haven Regional, returning Sat, Aug 8, priced at $244 found 19 hours ago
American Airlines
Wed, Sep 9 - Thu, Sep 17
MCO
Orlando Intl.
HPN
Westchester County
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 9 from Orlando Intl. to Westchester County, returning Thu, Sep 17, priced at $267 found 6 days ago