Head of the Harbor Holidays from £1,154

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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.
Hotel Stanford

Hotel Stanford

3 out of 5
Manhattan
Save 100% on your flight
Price was £1,824, price is now £1,154 per person
£1,154
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
8.6/10 Excellent! (2,741 reviews)
The staff was very accommodating and the room was comfortable. The breakfast was less than stellar, but otherwise, we would definitely stay here again.

Reviewed on 6 Jul 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,107, price is now £1,817 per person
£1,817
per person
29 Aug - 4 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Not the standard for a 1 Hotel property. I came in late and the fire alarm was falsely going off the entire time. No courtesy call and no zero attempt to accommodate the guests. The rooms need some work. Felt dingy and could use some serious touch ups and repairs. Just didn’t feel like the others.

Reviewed on 6 Jul 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £4,326, price is now £2,560 per person
£2,560
per person
29 Aug - 4 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on 5 Jul 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,056, price is now £1,255 per person
£1,255
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,652 reviews)
Amazing. Great service. Great location

Reviewed on 9 Jul 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,051, price is now £1,255 per person
£1,255
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,130 reviews)
The free breakfast is not worth it— very crowded and mediocre buffet. The room was nice, shower gets the whole bathroom floor wet. Great location to visit Times Square! Overall we would stay again!

Reviewed on 9 Jul 2026

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

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 £150 per night from 27 Jul to 28 Jul
£150
27 Jul - 28 Jul
includes taxes & fees
6.4/10 (1,678 reviews)
"I was treated very poorly. I had reserved a room with two beds, but when I arrived, they had already given it to someone else and didn't have any more available; they gave me a room with just one bed instead. My son had to sleep curled up on the floor on a cot. The staff at the front desk treated ..."

Reviewed on 8 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 £88 per night from 21 Jul to 22 Jul
£88
21 Jul - 22 Jul
includes taxes & fees
5.2/10 (1,061 reviews)
"No air conditioning in lobby upon check in Walk to room key didn’t work No restaurant on site closed room smelled I was very close to leaving and going someplace else very low bugdet and ghetto"

Reviewed on 8 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 £118 per night from 2 Aug to 3 Aug
£118
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,456 reviews)
"About a 10 min Uber to Hartford Healthcare Ampitheathre in Fairfield. Clean property, friendly staff, self-parking, outdoor pool and continental breakfast. All the basics needed for a stay in the area. Also there’s an amazing Italian restaurant about a 10-15 min walk away along with others. Would ..."

Reviewed on 8 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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 Harbour travel package cost?
Starting from an incredible £1,154, 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.

Explore a world of travel with Expedia

* 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.