Head of the Harbor Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Head of the Harbor

Price found within the past 48 hours. Click for updated prices.
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €1,778, price is now €1,142 per person
€1,142
per person
1 Oct - 4 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (719 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was €4,946, price is now €2,862 per person
€2,862
per person
14 Sept - 20 Sept
found 18 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9/10 Wonderful! (1,003 reviews)

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,872, price is now €1,717 per person
€1,717
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,623 reviews)
The experience was good. The staff was helpful and had a few restaurant suggestions handy. The hotel room a decent size and we had access to a private balcony. The balcony was a nice place for drinks and stargazing. There is a rooftop deck if you wanna be closer to the stars. I would stay here again and if your into nyc pizza there is a good spot across the street.

Reviewed on 31 Jul 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was €2,337, price is now €1,494 per person
€1,494
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,213 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,764, price is now €1,195 per person
€1,195
per person
24 Sept - 27 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,822 reviews)
Everything

Reviewed on 1 Aug 2026

Top hotels in Head of the Harbor

Hilton Long Island/Huntington

Hilton Long Island/Huntington

3.5 out of 5
598 Broad Hollow Rd Melville NY
Fully refundableReserve now, pay when you stay
The price is €169 per night from 16 Aug to 17 Aug
€169
16 Aug - 17 Aug
includes taxes & fees
Hilton Long Island/Huntington
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
The price is €147 per night from 30 Aug to 31 Aug
€147
30 Aug - 31 Aug
includes taxes & fees
Radisson Hotel Hauppauge-Long Island
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
Fully refundableReserve now, pay when you stay
The price is €87 per night from 1 Sept to 2 Sept
€87
1 Sept - 2 Sept
includes taxes & fees
5.2/10 (1,145 reviews)
"Parking lot in disrepair. Carpet in lobby old and musky smell. Lobby not welcoming not at all a good look."

Reviewed on 1 Aug 2026

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport
See all 1,073 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.

Stay near popular Head of the Harbor attractions

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

Avalon Park and Preserve

8.6/10 (4 reviews)
Explore the great outdoors at Avalon Park and Preserve, a lovely green space in Head of the Harbor. Attend a sporting event in this family-friendly area.
See properties

Frequently asked questions

How much does a Head of the Harbour holiday package cost?
You can grab a holiday package to this destination from €1,142 on Expedia. However, how much your holiday to Head of the Harbour costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Head of the Harbour?
January, February and March are the best times to look for cheap Head of the Harbour holiday packages. Opting to travel in quieter periods means you can generally find lower prices on hotels and flights.
How many days is enough for Head of the Harbour?
Generally, a handful of days is enough to go to the main sights during your Head of the Harbour holiday. But if you'd like to have time to unwind or go on day tours, consider extending your itinerary.
Is it worth booking a holiday package to Head of the Harbour?
Head of the Harbour has all the ingredients you need for a fantastic break — views, nature and walking trails are just the start. Whether you'd like to visit sights such as West Meadow Beach Historic District and Long Island Museum of American Art, History, and Carriages, or take the road less traveled, you'll have plenty to see and do on your Head of the Harbour holiday.
How to find the best Head of the Harbour package deals?
Finding a cheap Head of the Harbour package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" 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 even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Head of the Harbour holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the freedom to create a customised Head of the Harbour holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Head of the Harbour?
If you're planning a spur-of-the-moment Head of the Harbour adventure, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Head of the Harbour?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to holiday in Head of the Harbour.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will likely be the largest expense during your trip to Head of the Harbour.
  3. Work out your trip length: Consider how long you'd like to spend discovering Head of the Harbour. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Head of the Harbour holiday package that brings all your bookings together.

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