A tower with a spire, surrounded by wildflowers and greenery.

West End - West Side Vacations from $539

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Your West End - West Side Vacation

Our West End - West Side vacation packages are a fast and practical way to organize and reserve your next escape. Discover the true character of this unique neighborhood without the fuss of having to organize everything yourself. When it's time to get out and explore, you'll find plenty of awesome attractions nearby including Total Mortgage Arena, Hartford HealthCare Amphitheater and Seaside Beach. Visit one, two or all during your trip to West End - West Side. Expedia will help put your travel plans into action. Book your perfect West End - West Side vacation now.

The Latest West End - West Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A dimly lit bar with wooden furniture, hanging pendant lights, and a bar counter with a neon sign.
    Jan 14 - Jan 18

    Graduate by Hilton New Haven + Flight

    Downtown New Haven
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    Roundtrip • Miami (MIA) - New Haven (HVN)
    FLL - HVN • Nonstop HVN - FLL • Nonstop
    $617
    $539
    per traveler
    found 1 day ago
    Graduate by Hilton New Haven
  • A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.
    Dec 30 - Jan 3

    Heritage Hotel, Golf & Conference Center + Flight

    Southbury
    4 nights
    3.5 star property
    8.4/10 - Very good (1,004 reviews)
    "Staff is very friendly. Rooms and common areas are in need of updating, carpets in particular. Linens and bath are clean but room smelled a bit musty. On site tavern is fun. Lauren and Simon are great bartenders 😁. Breakfast is a bit pricey for a small buffet breakfast."
    Reviewed November 8, 2026
    Roundtrip • Miami (MIA) - New Haven (HVN)
    MIA - EWR • Nonstop EWR - MIA • Nonstop
    $731
    $554
    per traveler
    found 1 day ago
    Heritage Hotel, Golf & Conference Center
  • A modern kitchen with a central island, a dining area with chairs, and a view through large windows.
    Dec 30 - Jan 2

    Landing Apartments New Haven Near Dixwell + Flight

    Newhallville
    3 nights
    3.0 star property
    2.0/10 - (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 May 25, 2026
    Roundtrip • Fort Lauderdale (FLL) - New Haven (HVN)
    FLL - HVN • Nonstop HVN - FLL • Nonstop
    $1,185
    $1,004
    per traveler
    found 23 hours ago
    Landing Apartments New Haven Near Dixwell
  • A modern lounge area with a leather sofa, wooden coffee tables, and a large window providing natural light.
    Dec 30 - Jan 2

    Landing Apartments Downtown New Haven + Flight

    Downtown New Haven
    3 nights
    3.0 star property
    Roundtrip • Fort Lauderdale (FLL) - New Haven (HVN)
    FLL - HVN • Nonstop HVN - FLL • Nonstop
    $1,066
    $920
    per traveler
    found 23 hours ago
    Landing Apartments Downtown New Haven
  • A dining area with tables and chairs, large windows with curtains, and a view of a cityscape.
    Dec 30 - Jan 2

    Omni New Haven Hotel at Yale + Flight

    Downtown New Haven
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,122 reviews)
    "Perfect place to stay when visiting Yale! Just adjacent to the heart of campus and you feel so very well supported!!"
    Reviewed November 8, 2026
    Roundtrip • Fort Lauderdale (FLL) - New Haven (HVN)
    FLL - HVN • Nonstop HVN - FLL • Nonstop
    $848
    $747
    per traveler
    found 23 hours ago
    Omni New Haven Hotel at Yale

Where to stay in West End - West Side

Find the best West End - West Side areas and neighborhoods for the activities you enjoy most.
A rocky shoreline at sunset with the sun setting over the water.

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.

South End

While visiting South End, you might make a stop by sights like Seaside Park and Seaside Beach.

A city street lined with parked cars and tall buildings.
Photo by Mark Ferg
Open Photo by Mark Ferg

Downtown Bridgeport

If you're spending some time in Downtown Bridgeport, Bridgeport Downtown South Historic District and Total Mortgage Arena are top sights worth seeing.

North End

While visiting North End, you might make a stop by sights like Discovery Museum and The Adventure Park at Discovery Museum.

A lighthouse at night with a full moon in the sky.

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.

Discover the most popular places to visit in West End - West Side

Longfellow Park

Explore the great outdoors at Longfellow Park, a lovely green space in Bridgeport. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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West End - West Side Hotel Deals

A clear blue swimming pool with lounge chairs and umbrellas, surrounded by trees.

The Circle Hotel Fairfield

The Circle Hotel Fairfield
3.0 star property
2.2 mi from West End - West Side
8.8 out of 10, Excellent, (1,487 reviews)
$152 nightly
The price is $175
Dec 6 - Dec 7
Total with taxes and fees
The Circle Hotel Fairfield
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.