Head of the Harbor Holidays from £1,373

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Your Head of the Harbour Holiday

Our Head of the Harbour holiday packages offer countless opportunities to enjoy new sights, sounds and tastes. And with all your travel plans worked out, you can chill out and enjoy your city getaway without a care in the world. Fill your days with tours of Stony Brook University, Lake Ronkonkoma and Stonebridge Golf Links and Country Club, some of the things you simply have to see during a trip to Head of the Harbour. Don't delay your visit to this city any longer. Your perfect Head of the Harbour holiday is a few quick clicks away with Expedia.

Top Head of the Harbor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Manhattan SoHo Village

Four Points by Sheraton Manhattan SoHo Village

3 out of 5
Manhattan
Price was £2,981, price is now £1,373 per person
£1,373
per person
19 Oct - 23 Oct
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
8.4/10 Very Good! (1,007 reviews)
Very kind and helpful staff.

Reviewed on 26 Aug 2025

Washington Square Hotel

Washington Square Hotel

3.5 out of 5
Manhattan
Price was £3,061, price is now £1,410 per person
£1,410
per person
19 Oct - 23 Oct
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,115 reviews)
Room was small but perfect for our needs. Shower was spa-level awesome. Staff was great. No fridge in our room if that’s important to you. Loved that the windows opened to feel connected to Washington Square vibe.

Reviewed on 24 Aug 2025

The Merchant Hotel Lower East Side, Sonder by Marriott Bonvoy

The Merchant Hotel Lower East Side, Sonder by Marriott Bonvoy

3.5 out of 5
Manhattan
Price was £2,904, price is now £1,428 per person
£1,428
per person
19 Oct - 23 Oct
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (34 reviews)
Loved staying here. Know that you’re in basically an ApartHotel but the rooms are lovely, the staff great when you need something or have an issue. And you’re close to some of the best restaurants in Manhattan!

Reviewed on 18 Aug 2025

Moxy NYC Lower East Side

Moxy NYC Lower East Side

4 out of 5
Manhattan
Price was £2,896, price is now £1,456 per person
£1,456
per person
19 Oct - 23 Oct
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,684 reviews)
All the restaurants and bars in the property

Reviewed on 21 Aug 2025

Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Manhattan
Price was £3,226, price is now £1,678 per person
£1,678
per person
19 Oct - 23 Oct
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
Hotel was undergoing some renovations but all in all was great for the price.

Reviewed on 18 Aug 2025

Head of the Harbour Essential Information

Language
English
Currency
U.S dollars
Closest Airport
MacArthur Airport (ISP)
Population
1,500
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Harmony Vineyards, Short Beach and Avalon Park and Preserve

Top hotels in Head of the Harbor

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
The price is £93 per night from 1 Sept to 2 Sept
£93
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,185 reviews)
Stay here
"Everything was great. Breakfast iscincluded"

Reviewed on 25 Aug 2025

Hampton Inn Long Island-Brookhaven
Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

3.5 out of 5
3635 Express Dr N, Islandia, NY
Fully refundableReserve now, pay when you stay
The price is £107 per night from 14 Sept to 15 Sept
£107
14 Sept - 15 Sept
includes taxes & fees
8/10 Very Good! (1,180 reviews)
"everything was good"

Reviewed on 23 Aug 2025

Jake's 58 Casino Hotel - Adult Only
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 £81 per night from 1 Sept to 2 Sept
£81
1 Sept - 2 Sept
includes taxes & fees
6.6/10 (1,305 reviews)
"Oils breakfast oy"

Reviewed on 23 Aug 2025

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
See all 1,079 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Head of the Harbour travel package cost?
Starting from an incredible £1,373, you can handcraft your own Head of the Harbour travel package. Simply bundle hotels, flights and rental cars and be rewarded with discounts.
If I'm not able to travel, can I cancel my Head of the Harbour travel package?
Because we understand life is full of surprises, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've booked your Head of the Harbour travel package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Head of the Harbour?
Simply by bundling. Hotels, flights and rental cars — combine whatever you need into a Head of the Harbour holiday package to save tons of cash. Score even more deals when you add extras such as day tours to your booking. But that's not the only good part. You have the freedom to tailor your holiday your way. We offer over 550 airlines and 1,000,000 hotels across the globe, so that everyone has a chance to travel and live out those holiday fantasies.
Does Expedia offer Book Now, Pay Later Head of the Harbour holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a terrific getaway without draining your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's convenient monthly instalment plans. If making small repayments each month works for you, pick this option at checkout.
  • Pay in instalments holidays: If you want to pay off your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Hitting the "book now" button is easier with this option. Just put down a small deposit on your escape and then start packing your suitcase.

Where should I stay in Head of the Harbour?
Head of the Harbour features a number of fascinating places to explore, including Harmony Vineyards. Lock in a hotel nearby and make sightseeing easier.
How far in advance should I book my Head of the Harbour holiday?
It's hard to pick the perfect time for airfares, but we generally say the earlier, the better. Most international journeys on Expedia become available to compare up to a year in advance. If you can't book ahead, don't fret. Low prices appear from time to time just weeks before departure dates.
What does an Expedia Head of the Harbour travel package include?
Travel packages include flights, rental cars and hotels, but you can mix and match them to create your ideal Head of the Harbour escape. You can also add on experiences and activities once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Head of the Harbour travel package?
A travel package can be easier on the bank balance than separately booking everything you need for your adventure. For example, bundle your hotels, flights and rental cars and save a packet. Whatever sort of holiday you're planning, you'll find a package to suit your budget.
Can I choose my airline with a Head of the Harbour Expedia travel package?
Most definitely. Expedia has access to more than 550 partner airlines across the globe, so you can tailor your Head of the Harbour escape according to your travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.