Head of the Harbor Packages (Flight + Hotel)

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Top hotels in Head of the Harbor

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 ฿5,214 per night from 8 Jul to 9 Jul
฿5,214
฿5,957 total
8 Jul - 9 Jul
includes taxes & fees
6.4/10 (1,670 reviews)
"I cannot say perfect but it’s ok. If you really can not find another hotel and you can try that one."

Reviewed on 5 Jul 2026

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 ฿3,424 per night from 8 Jul to 9 Jul
฿3,424
฿3,912 total
8 Jul - 9 Jul
includes taxes & fees
5.2/10 (1,048 reviews)
"Upon arrival driving from n.c. I arrived earlier then 3 pm and charged 50.00 for early arrival. Outside the side entrance multiple plates with food rotting in the sun. Place needs a serious upgrade."

Reviewed on 4 Jul 2026

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road Fairfield CT
Fully refundable
The price is ฿4,485 per night from 2 Aug to 3 Aug
฿4,485
฿5,490 total
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,445 reviews)
"Staff were very friendly. Room was clean and beds were comfortable. Very well run. Continental breakfast even had real orange juice and not just concentrate. They really care about the little things too"

Reviewed on 4 Jul 2026

The Circle Hotel Fairfield
See all 1,058 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.
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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.

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