A coastal town with a marina filled with boats, a lighthouse, and a hill with buildings.

Head of the Harbor Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Head of the Harbor vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Sept 11 - Sept 14

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    3 nights
    4.0 star property
    9.2/10 - Wonderful (3,764 reviews)
    "The rooms were clean and spacious for an nyc hotel. The staff were all very nice."
    Reviewed July 19, 2026
    Roundtrip Ottawa (YOW) - New York (JFK)
    YOW - LGA1 stop LGA - YOW1 stop
    CA $2,030
    CA $1,282
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • Aug 27 - Aug 30

    Mandarin Oriental, New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (652 reviews)
    "Amazing hotel, staff make the whole experience, bar is great. Reception and concierge team are excellent, in particular Lauren who made check in a breeze. Gym and pool are excellent for a New York hotel."
    Reviewed June 21, 2026
    Roundtrip Toronto (YTO) - New York (JFK)
    YYZ - LGANonstop JFK - YYZNonstop
    CA $2,831
    CA $1,715
    per traveller
    found 1 day ago
    Mandarin Oriental, New York
  • Sept 2 - Sept 5

    1 Hotel Brooklyn Bridge + Flight

    Brooklyn
    3 nights
    5.0 star property
    9.0/10 - Wonderful (1,005 reviews)
    Roundtrip Toronto (YTO) - New York (JFK)
    YYZ - JFKNonstop JFK - YYZ1 stop
    CA $4,207
    CA $2,657
    per traveller
    found 17 hours ago
    1 Hotel Brooklyn Bridge
  • Sept 3 - Sept 7

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    4 nights
    4.0 star property
    9.0/10 - Wonderful (3,217 reviews)
    Roundtrip Hamilton (YHM) - New York (JFK)
    YHM - EWR1 stop EWR - YHM1 stop
    CA $2,622
    CA $1,734
    per traveller
    found 3 hours ago
    Hotel Riu Plaza New York Times Square
  • Oct 12 - Oct 16

    Candlewood Suites New York City-Times Square by IHG + Flight

    Manhattan
    4 nights
    2.5 star property
    8.6/10 - Excellent (2,089 reviews)
    Roundtrip Toronto (YTO) - New York (JFK)
    YTZ - LGANonstop LGA - YYZNonstop
    CA $2,013
    CA $1,358
    per traveller
    found 1 day ago
    Candlewood Suites New York City-Times Square by IHG

Discover the most popular places to visit in Head of the Harbor

Head of the Harbor Hotel Deals

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.

Frequently Asked Questions

How much does a Head of the Harbour vacation package cost?

You can grab a vacation package to this popular destination from CA $1,282 on Expedia. But how much your vacation to Head of the Harbour costs will depend on factors like the length of stay, season and hotel choice.

What are the cheapest months to go to Head of the Harbour?

January, February and March are great times to search for cheap Head of the Harbour vacation packages. Travelling in less busy months means you can generally find lower prices on flights and accommodations.

How many days is enough for Head of the Harbour?

Usually, a handful of days is enough to explore the top sights during your Head of the Harbour vacation. But if you'd like to have more time to relax or go on day tours, think about extending your itinerary.

Is it worth booking a vacation package to Head of the Harbour?

Head of the Harbour has all the ingredients you need for an amazing break — views, nature and walking trails are just the start. Whether you'd like to check out sights like West Meadow Beach Historic District and Long Island Museum of American Art, History, and Carriages, or venture off the beaten track, there's plenty to see and do on your Head of the Harbour vacation.

How to find the best Head of the Harbour package deals?

Landing a cheap Head of the Harbour package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Head of the Harbour package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.

Is it cheaper to book a Head of the Harbour vacation as a package?

Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a customized Head of the Harbour vacation by choosing your favourite accommodation type, airline and car class.

When to book a vacation package to Head of the Harbour?

If you have your Head of the Harbour travel dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.

How to plan a trip to Head of the Harbour?

  1. Choose your travel dates: What you want to do in Head of the Harbour and your preferred season will help you decide when to go.
  2. Budget wisely: Besides the cost of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that could crop up during your trip to Head of the Harbour.
  3. Decide your trip length: Think about how long you want to spend discovering Head of the Harbour. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Head of the Harbour vacation package.