Head of the Harbor Holidays

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Top Flight + Hotel Deals in Head of the Harbor

Price found within the past 48 hours. Click for updated prices.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
1 Sept - 7 Sept
found 19 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
7.6/10 Good! (796 reviews)
Great location. Spacious room.

Reviewed on 6 May 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
1 Sept - 7 Sept
found 19 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9.8/10 Exceptional! (1,199 reviews)
We enjoyed the location and the staff at this property. This is the second time we stayed there.

Reviewed on 16 Jun 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
18 Jul - 25 Jul
found 1 hour ago
Return flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,614 reviews)
Just as described. Clean, spacious room, terrific restaurant. Friendly, professional staff.

Reviewed on 18 Jun 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
per person
1 Sept - 7 Sept
found 19 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9/10 Wonderful! (1,511 reviews)
If you want to be in Times Square this is the perfect location, has great restaurants and an amazing rooftop bar. As for the rooms, this hotel is not 5 * more like 4 at best. The rooms are not as shown on marketing materials but much smaller and barely a window. I felt very confined in the room and had to get a different room with more windows so I didn't feel trapped.

Reviewed on 12 Jun 2025

Hotel Indigo Lower East Side New York by IHG

Hotel Indigo Lower East Side New York by IHG

4.5 out of 5
Manhattan
per person
18 Jul - 25 Jul
found 1 hour ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,511 reviews)
Great location! close to F train for easy access to BK or midtown. Good eats and bars walking distance. Hotel staff was friendly and helpful. I enjoyed my city view room, it was spacious and bed was comfortable. I Will be back!

Reviewed on 18 Jun 2025

Top hotels in Head of the Harbor

Hyatt Regency Long Island
Hyatt Regency Long Island
4 out of 5
1717 Motor Parkway, Hauppauge, NY
The price is €118 per night from 25 Jun to 26 Jun
€118
25 Jun - 26 Jun
includes taxes & fees
8.2/10 Very Good! (1,006 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 €97 per night from 22 Jun to 23 Jun
€97
22 Jun - 23 Jun
includes taxes & fees
6.8/10 (1,228 reviews)
"A great place if you are looking for quite/decent room to sleep. As a traveling nurse, I needed a place to sleep and this place met that need. Breakfast was not great, I like hot breakfast but that was missing. I do not have the leisure to explore other amenities they claim they have. Overall, I ..."

Reviewed on 16 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
The price is €126 per night from 23 Jun to 24 Jun
€126
23 Jun - 24 Jun
includes taxes & fees
8.6/10 Excellent! (1,100 reviews)
"No butter spray for waffle maker for two mornings & staff response was they don’t have any. Everyone’s waffles were sticking and making a mess. Not sure why staff handling kitchen area couldn’t figure that out?? Get a new waffle iron or provide Pam spray. Third morning - there was some spray…"

Reviewed on 15 Jun 2025

Hampton Inn Long Island-Brookhaven
See all 1,076 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 from €989 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.