Head of the Harbor Vacation Packages

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Your Head of the Harbor Vacation

Our Head of the Harbor vacation packages offer countless opportunities to enjoy new sights, sounds and tastes. And with all your travel plans worked out, you can chill out and enjoy your city getaway without a care in the world. Fill your days with tours of Stony Brook University, Lake Ronkonkoma and Stonebridge Golf Links and Country Club, some of the things you simply have to see during a trip to Head of the Harbor. Don't delay your visit to this city any longer. Your perfect Head of the Harbor vacation is a few quick clicks away with Expedia.

Top Head of the Harbor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,429 reviews)
The room was poorly cleaned, as usual unfortunately for my experience with Hyatt in general. Otherwise no complaints, and view was great! Public transportation was right there as well!

Reviewed on Jul. 24, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Very tiny room with no good light, could barely see there. Also blanket doesnt have a cover up. No proper bathroom.

Reviewed on Jul. 17, 2025

Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (NYC)
8.8/10 Excellent! (200 reviews)
Placed in room at end of hall, overlooking trash dumpsters. Had excessive noise in the mornings and then on last night had loud noise

Reviewed on Jul. 24, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

New York Marriott Downtown

New York Marriott Downtown

4 out of 5
Manhattan
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Great location, convenient to the train station, enjoyed the gym, easy to find places to eat, and my family of 15 visiting New York loved our stay! Only cons- bed was small/not too comfortable & towels had a musty smell like they weren’t dried fully.

Reviewed on Jul. 15, 2025

Ready to book your vacation to Head of the Harbor?

 

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Head of the Harbor Hotel Deals

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
The price is CA $185 per night from Jul 28 to Jul 29
CA $185
CA $212 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (1,158 reviews)
"Perfect location with restaurants and food store."

Reviewed on Jul. 23, 2025

Hampton Inn Long Island-Brookhaven
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

3 out of 5
10 Aero Rd, Bohemia, NY
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Aug 17 to Aug 18
CA $132
CA $150 total
Aug 17 - Aug 18
includes taxes & fees
6.8/10 (1,272 reviews)
"Ok place needs to be updated"

Reviewed on Jul. 18, 2025

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundable
The price is CA $174 per night from Aug 4 to Aug 5
CA $174
CA $200 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (1,387 reviews)
"Very clean. Quiet. Nice grounds. Close to amenities. Friendly people. Everything was great except the bed was too hard for my liking. Would stay again though"

Reviewed on Jul. 23, 2025

The Circle Hotel Fairfield
See all 1,070 properties in Head of the Harbor
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.
All Inclusive Vacations
All Inclusive Vacations
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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 $828 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.

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