Head of the Harbor Holidays

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Head of the Harbor Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
19 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
My company is headquartered in Tribeca, so the location is perfect. The hotel is QUIET as the street isn't a major thoroughfare, and there are no bars on the block. Easy access to transportation, and great dining.

Reviewed on 16 Aug, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
19 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
The server was so good specially the luggage man

Reviewed on 16 Aug, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
19 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (3,368 reviews)
Great experience from check in to check out. I observed the frontdesk representatives kept an eye on 2 little child while their parents stepped away. He and the security kept a close eyes on the kids to ensure they didn't leave the lobby by themselves and contacted their parents to return asap to pick up their child. Thank you for ensuring safety of the little ones. Very polite services from everyone in the hotel, especially the breakfast arrangement is awesome! Great processes involved to ensure efficiency during the busy morning. Of course the breakfast is 100% , great food, good quality with lots of options. Last but not least, thanks for the champaign, what a great surprise for the family and celebrations.

Reviewed on 15 Aug, 2025

W New York - Times Square

W New York - Times Square

4.5 out of 5
Manhattan
per person
19 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.6/10 Excellent! (1,740 reviews)
We had a great time at the W Times Square. Ish was simply fantastic, he made our checkin process easy and explained the property in a funny and friendly way. We were able to go to the TMPL gym and got our complimentary drinks. He also signed us up to become Marriott members, so we’re looking ahead to a long time relationship with the chain. Ish, you’re amazing and you deserve a HUGE raise. Best, David and Alejandro from Vegas

Reviewed on 16 Aug, 2025

The Dominick

The Dominick

5 out of 5
Manhattan
Save 100% on your flight
per person
19 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
Perfect location for the girls trip with my 15year old daughter. Soho shopping was great! The pool was fantastic and the location was less than a block to the subway. We rode the subway all week and never felt unsafe. Excellent hotel, we will be back!

Reviewed on 14 Aug, 2025

Top hotels in Head of the Harbor

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 1 Sept to 2 Sept
S$135
1 Sept - 2 Sept
includes taxes & fees
6.6/10 (1,301 reviews)
"Everyone was friendly and the hotel was clean.I would stay here again."

Reviewed on 15 Aug, 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$161 per night from 2 Sept to 3 Sept
S$161
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (1,169 reviews)
"There isnt much parking but besides that everything was clean just a little out of date. But over all staff and hotel were great."

Reviewed on 13 Aug, 2025

Hampton Inn Long Island-Brookhaven
Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG

2.5 out of 5
3131 Nesconset Hwy, Centereach, NY
Fully refundable
The price is S$229 per night from 1 Sept to 2 Sept
S$229
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"The morning breakfast was great! Thank you to Arcenia she is very attentive to the service!!"

Reviewed on 15 Aug, 2025

Holiday Inn Express Stony Brook by IHG
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 S$2,171 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.