Bridgeport(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Bridgeport, the Holiday Inn Bridgeport Downtown stands out as a top choice for families, offering spacious rooms, an indoor pool, and complimentary breakfast. Located near the Bridgeport Municipal Building and the Connecticut River, it provides easy access to family attractions like the Connecticut Science Center and Bridgeport Public Library. Its kid-friendly amenities and central location make it ideal for exploring the city with children.

The Hutton Hotel is Bridgeport’s premier boutique property, housed in a restored 19th-century textile mill. With its industrial-chic design, original machinery displays, and art-filled common areas, it blends historical character with modern luxury. The rooftop bar offers panoramic views of the city skyline, while curated events such as live jazz nights and local author talks deepen guests’ connection to the community’s cultural heritage.

Explore the Old Bridgeport Historic District along Congress Avenue, where you’ll find preserved architecture, including the Hartford Courant Building and St. Mary’s Church. Attend the annual Bridgeport Arts & Crafts Festival, showcasing regional artisans and traditional crafts. Visit the Bridgeport Museum of Art, which features rotating exhibitions of local talent, offering a deep dive into the area’s artistic identity and community spirit.

Westside offers a tranquil retreat perfect for solo travelers, nestled near Barnum Museum and the serene Greenfield Hill Cemetery. Stay at The Westside Inn, known for its quiet rooms, private courtyard, and free Wi-Fi. Begin your day with a walk through Saw Mill River Park, enjoying nature amidst urban life—ideal for reflection, writing, or simply unwinding.

Yes, many hotels in Bridgeport provide shuttle services or partner with CT Transit for easy access to key sites like the Museum of Contemporary Art, Barnum Museum, and Bridgeport Harbor. The Bridgeport Marriott and Hampton Inn Bridgeport feature guest concierge desks to assist with tours and transit planning. Some also offer bike rentals, enabling guests to explore scenic riverside trails and waterfront paths at their own pace.

The Hutton Hotel exemplifies the fusion of past and present. Originally a 19th-century textile factory, it now features exposed brick walls, reclaimed wood interiors, and modern art installations. The lobby showcases original looms as sculptures, while guest rooms blend vintage industrial elements with sleek furnishings. Regular events like live jazz performances and local artist meetups keep the atmosphere vibrant and culturally rich.

Hutton Kitchen at The Hutton Hotel serves elevated New England fare, including Connecticut-style steak and blue crab bisque, paired with locally brewed craft beer. Meanwhile, Riverfront Bistro at Holiday Inn Bridgeport Downtown specializes in fresh seafood platters and classic American burgers, with outdoor seating overlooking the Connecticut River—perfect for enjoying regional flavors with a view.

For value-conscious travelers, Comfort Inn Bridgeport offers affordable rates just off I-95, with free breakfast, a fitness center, and proximity to Downtown Shopping Plaza and Lion’s Park. It’s ideal for weekend getaways or business trips, providing reliable comfort without compromising on convenience or cleanliness—making it a smart pick for short stays.

Downtown Bridgeport pulses with energy, home to venues like The Shubert Theatre, ArtWalk Gallery, and Café 318. Every Friday, Friday Night Live brings live music from local bands and indie artists. The rooftop bar at The Hutton Hotel often hosts open mic nights and DJ sets, creating a lively yet intimate atmosphere that captures the city’s creative heartbeat.

Yes, Bridgeport Marriott and Hampton Inn Bridgeport offer fully equipped meeting spaces, including a 100-person conference room, high-speed internet, and AV support. On-site event planners help organize agendas, catering, and logistics. Nearby, the Metroplex Convention Center accommodates larger gatherings, making Bridgeport a practical destination for conferences and team retreats across Connecticut’s southern region.