Head of the Harbor Vacations

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Find the Best Head of the Harbor Vacation Packages

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 NT$3,990 per night from Nov 15 to Nov 16
NT$3,990
NT$4,559 total
Nov 15 - Nov 16
includes taxes & fees
6.6/10 (1,899 reviews)
"Staff member swearing to manager about no support in front of me. Complaining about her job. While getting breakfast cook leaves area will eggs cooking in pan burning and sets off building for alarm as people waking up. I left a day early. Also 3 machined in gym broken and missing most weights"

Reviewed on 2026/11/2

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 NT$3,814 per night from Nov 30 to Dec 1
NT$3,814
NT$4,357 total
Nov 30 - Dec 1
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 NT$5,509 per night from Nov 3 to Nov 4
NT$5,509
NT$6,662 total
Nov 3 - Nov 4
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 2026/11/1

The Circle Hotel Fairfield
See all 1,036 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 Harbor vacation package cost?
You can grab a vacation package to this destination on Expedia. However, how much your vacation to Head of the Harbor costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Head of the Harbor?
January, February and March are the best times to look for cheap Head of the Harbor vacation 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 Harbor?
Generally, a handful of days is enough to go to the main sights during your Head of the Harbor vacation. But if you'd like to have time to unwind or go on day tours, consider extending your itinerary.
Is it worth booking a vacation package to Head of the Harbor?
Head of the Harbor 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 Harbor vacation.
How to find the best Head of the Harbor package deals?
Finding a cheap Head of the Harbor 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 Harbor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Head of the Harbor vacation as a package?
Expedia vacation 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 customized Head of the Harbor vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Head of the Harbor?
If you're planning a spur-of-the-moment Head of the Harbor 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 Harbor?

  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 vacation in Head of the Harbor.
  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 Harbor.
  3. Work out your trip length: Consider how long you'd like to spend discovering Head of the Harbor. 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 Harbor vacation 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.