Head of the Harbor Holidays from AU$992

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Your Head of the Harbour Holiday

The fascinating city of Head of the Harbour is calling your name. Delve into everything from its highlights to its hidden gems with a Head of the Harbour holiday package that's tailored to you. If your trip to Head of the Harbour includes a little sightseeing, take in well-known attractions like Stony Brook University, Lake Ronkonkoma and Stonebridge Golf Links and Country Club. No matter your travel plans or budget, organising a tailored Head of the Harbour holiday is simple with Expedia.

The Latest Head of the Harbor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Queens
Price was AU$1,405, price is now AU$992 per person
AU$992
per person
14 Dec - 17 Dec
found 13 hours ago
Return direct flight included
Nashville (BNA) to New York (JFK)
7.2/10 Good! (536 reviews)
First things first: if you're staying less than a week, they will add a nightly surcharge to your bill. This was not listed on Expedia. There is rarely anyone at the front desk. Everything is done electronically. It's really hard to check in by phone, and because of location, coming back at night can feel a little scary. The place is not as well kept up as previous owners had kept it. There are stains in the hall rugs. Photo-sensitive hall lights are late coming on. Two lamps in my room did not work. Don't expect maid service during your stay, nor was the room service all that complete. There were dishes in the dishwasher when I checked in. The HVAC unit is inconsistent. It resets the temperature on its own, so if you like to sleep cold, be prepared to wake up in a sweat.

Reviewed on 1 Nov 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was AU$2,299, price is now AU$1,446 per person
AU$1,446
per person
14 Dec - 17 Dec
found 15 hours ago
Return flight included
Nashville (BNA) to New York (JFK)
9.4/10 Exceptional! (275 reviews)

Royalton New York

Royalton New York

4 out of 5
Manhattan
Price was AU$1,564, price is now AU$1,073 per person
AU$1,073
per person
14 Dec - 17 Dec
found 1 day ago
Return flight included
Nashville (BNA) to New York (JFK)
7.8/10 Good! (1,005 reviews)

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was AU$8,102, price is now AU$5,668 per person
AU$5,668
per person
25 Dec - 1 Jan
found 1 hour ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was AU$15,841, price is now AU$11,341 per person
AU$11,341
per person
25 Dec - 1 Jan
found 1 hour ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

Head of the Harbor Holiday

Head of the Harbour Essential Information

Language
English
Currency
U.S dollars
Closest Airport
MacArthur Airport (ISP)
Population
1,500
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Harmony Vineyards, Short Beach and Avalon Park and Preserve

Our pick of the best Head of the Harbor Hotel Deals

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 AU$199 per night from 15 Nov to 16 Nov
AU$199
15 Nov - 16 Nov
includes taxes & fees
Radisson Hotel Hauppauge-Long Island
Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 out of 5
2050 Express Dr S Hauppauge NY
Fully refundable
The price is AU$190 per night from 30 Nov to 1 Dec
AU$190
30 Nov - 1 Dec
includes taxes & fees
Holiday Inn Express Hauppauge-Long Island
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road Fairfield CT
Fully refundableReserve now, pay when you stay
The price is AU$291 per night from 16 Nov to 17 Nov
AU$291
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (1,478 reviews)
"The young woman at the Front Desk was rude and dismissive. They are closing this hotel in a few months and you could tell by their attitude. On top of that advertise the breakfast to be a lot better than it is in the room is rundown. Is basically a motel from the 50s or 60s. The refrigerator in room ..."

Reviewed on 1 Nov 2026

The Circle Hotel Fairfield
See all 1,039 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.
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beach holidays
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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 AU$992 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.