Head of the Harbor Vacations from $625
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Your Head of the Harbor Vacation
Our Head of the Harbor vacation 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 Harbor. Don't delay your visit to this city any longer. Your perfect Head of the Harbor vacation is a few quick clicks away with Expedia.
The Latest Head of the Harbor vacation packages
Price found within the past 48 hours. Click for updated prices.
Sound View Greenport
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..
Reviewed on Jul 10, 2025
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Harmony Vineyards
5/5(1 review)
You can enjoy a tasting or tour at Harmony Vineyards during your travels to Head of the Harbor. Attend a sporting event in this family-friendly area.
Head of the Harbor Hotel Deals
Hampton Inn Long Island-Brookhaven
2000 North Ocean Ave., Farmingville, NY
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $150 total per night from Aug 3 to Aug 4
$150 total
Aug 3 - Aug 4
Total includes taxes and fees
8.6/10 Excellent! (1,146 reviews)
"I loved the stay except for having to pay for parking! If we paid for a room, we should be given a sticker for our car. Don’t punish us because other people park in your parking lot!"
Reviewed on Jul 9, 2025
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
10 Aero Rd, Bohemia, NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Aug 3 to Aug 4
$112 total
Aug 3 - Aug 4
Total includes taxes and fees
6.8/10 (1,255 reviews)
"Great staff great place"
Reviewed on Jul 15, 2025
The Circle Hotel Fairfield
417 Post Road, Fairfield, CT
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $194 total per night from Aug 4 to Aug 5
$194 total
Aug 4 - Aug 5
Total includes taxes and fees
8.8/10 Excellent! (1,394 reviews)
"Great location"
Reviewed on Jul 15, 2025
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.
Find the Best Head of the Harbor Vacation Packages
Head of the Harbor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | MacArthur Airport (ISP) |
Population | 1,500 |
Top Sights | Harmony Vineyards, Short Beach and Avalon Park and Preserve |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.