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

West End - West Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $4,200 when you book a flight and hotel together*

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The Latest West End - West Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with two beds, a red chair, a nightstand with a lamp, and framed artwork on the wall.
    Dec 23 - Dec 27

    Quality Suites Stratford + Flight

    Stratford
    4 nights
    2.5 star property
    8.2/10 - Very good (1,002 reviews)
    "It was convenient to town and shopping. Our air conditioner leaked all over the rug and it was soaking wet. Pillows were awful. We would not stay there again."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - EWR • Nonstop EWR - YYZ • Nonstop
    CA $890
    CA $888
    per traveller
    found 16 hours ago
    Quality Suites Stratford
  • A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.
    Dec 14 - Dec 17

    Beechmont - Perfect for Family Retreat! + Flight

    North End
    3 nights
    5.0 star property
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,120
    CA $1,858
    per traveller
    found 16 hours ago
    Beechmont - Perfect for Family Retreat!
  • A room with a view of the ocean at sunset, a dining table with plates and glasses, and a wicker chair.
    Dec 24 - Dec 30

    The Surfside Hotel + Flight

    Lordship
    6 nights
    2.0 star property
    9.2/10 - Wonderful (229 reviews)
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - EWR • Nonstop LGA - YYZ • Nonstop
    CA $1,263
    CA $1,118
    per traveller
    found 8 hours ago
    The Surfside Hotel
  • A hotel lobby with a reception desk, a television mounted on the wall, a trash can, and a seating area with orange chairs and a table.
    Dec 27 - Jan 2

    Motel 6 Milford, CT + Flight

    Milford
    6 nights
    2.0 star property
    6.6/10 - (1,066 reviews)
    Roundtrip • Saskatoon (YXE) - New Haven (HVN)
    YXE - EWR • 1 stop EWR - YXE • 2 stops
    CA $1,809
    CA $1,766
    per traveller
    found 1 hour ago
    Motel 6 Milford, CT

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
3.5 km from West End - West Side
8.8 out of 10, Excellent, (1,487 reviews)
The price is CA $202
CA $247 total
includes taxes & fees
Dec 6 - Dec 7
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.
See all properties in West End - West Side

Frequently Asked Questions

How much does a West End - West Side vacation package cost?

Handcraft your West End - West Side package from only CA $888. Choose from any combination of flights, hotels and rental cars to create the trip you've been dreaming of. Don't forget to add on some activities and experiences!

How do I get a cheap travel package to West End - West Side?

Combine your bookings with Expedia to save big bucks on your next getaway. With more than 550 airlines and 1,000,000 hotel options around the globe, your West End - West Side vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not throw in one or two interesting tours and experiences? It's an easy way to unlock even more bargains. The vacation you've always dreamed of in West End - West Side is much closer than you thought!

Where should I stay in West End - West Side?

A vacation in West End - West Side isn't complete without paying a visit to Hartford HealthCare Amphitheater, Total Mortgage Arena and Seaside Beach. Stay close to these top attractions and make sightseeing easy.

What are the top hotels in West End - West Side?

Classic Deluxe 5bedroom 2baths With Backyard is one of West End - West Side's leading hotels. Book a room here and you'll slumber peacefully knowing you're in excellent hands.

How far in advance should I book my West End - West Side vacation?

Search Expedia to compare airfares as early as possible. You can normally purchase a ticket up to a year prior to departure. If you can't find your preferred carrier, or you've left things to the last moment, don't worry. Cheap tickets to West End - West Side sometimes appear a few weeks before departure.

What does an Expedia West End - West Side travel package include?

Rental cars, flights and hotels, or any combination of them — it's your pick! Whether you're venturing to West End - West Side with the family or adventuring solo, there's a package to suit every budget and style. Once you've made your booking, why not add on a couple of tours as well?

What should I know before booking a West End - West Side travel package?

So many places to travel to, so many things to do. With a package, you can tick more of them off your list. Combine your hotels, flights and rental cars and get ready to save.

Can I choose my airline with a West End - West Side Expedia vacation package?

Definitely. Expedia has more than 550 partner airlines to choose from around the globe. With such a huge range of choice, finding the perfect carrier to fly you to West End - West Side will be easy.

If I'm not able to travel, can I cancel my West End - West Side vacation package?

It's difficult to predict what the future holds, so it's comforting to know that you can change or cancel your West End - West Side vacation package. If you made your booking in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.