Head of the Harbor Holidays

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Top hotels in Head of the Harbor

Hyatt Regency Long Island
Hyatt Regency Long Island
4 out of 5
1717 Motor Parkway, Hauppauge, NY
Fully refundableReserve now, pay when you stay
The price is S$175 per night from 19 Jun to 20 Jun
S$175
19 Jun - 20 Jun
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Clean and fragrance free, will visit again, thank you"

Reviewed on 8 Jun, 2025

Hyatt Regency Long Island
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 S$135 per night from 15 Jun to 16 Jun
S$135
15 Jun - 16 Jun
includes taxes & fees
6.8/10 (1,222 reviews)
Good Overall, Some Amenities Out of Service
"The room was clean and spacious. The spa was not functional, and none of the ice makers worked. I went to every floor and they were all out of service. The breakfast was great, and the staff was friendly."

Reviewed on 10 Jun, 2025

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Hampton Inn Long Island-Brookhaven
Hampton Inn Long Island-Brookhaven
2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
Fully refundableReserve now, pay when you stay
The price is S$180 per night from 15 Jun to 16 Jun
S$180
15 Jun - 16 Jun
includes taxes & fees
8.6/10 Excellent! (1,094 reviews)
"Great little spot in the middle of Jamestown about 40 minutes from Niagara Falls and suny Fredonia"

Reviewed on 7 Jun, 2025

Hampton Inn Long Island-Brookhaven
See all 1,075 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.

Frequently asked questions

How much does a Head of the Harbour holiday package cost?
You can grab a holiday package to this destination 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.