Head of the Harbor Vacations from $266

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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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $577, price is now $266 per person
$266
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,030 reviews)
The view isn't the best. It's nice but has a hig water tower right in front of the windows. Nothing you can do about it...

Reviewed on Oct 27, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $660, price is now $336 per person
$336
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,359 reviews)
Riu Plaza Manhattan was the perfect location and exceeded expectations.. Room was very quiet,no street noise! Staff was very helpful. My fourth stay at this hotel,never disappoints.

Reviewed on Oct 27, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $786, price is now $414 per person
$414
per person
Jan 15 - Jan 19
just found
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Stayed in for one night and the room was beautiful. The bed was beyond comfortable and clean. From the check in to check out, staff was very helpful. 100% will recommend.

Reviewed on Oct 25, 2025

Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
Price was $605, price is now $329 per person
$329
per person
Dec 30 - Jan 2
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,020 reviews)
Great stay for an early morning flight out of Newark! Highly recommend it if you are trying to get out of Manhattan and want a reasonably priced hotel with great amenities. Restaurants, room service, and the bar lounge are all open until late.

Reviewed on Oct 27, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $603, price is now $337 per person
$337
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.8/10 Exceptional! (1,377 reviews)
Every time I go to NY this is my hotel of choice. The staff is amazing!!! The location can’t be beat, China town to one side, little Italy to the other and next to the subway.

Reviewed on Oct 26, 2025

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Discover the most popular places to visit in Head of the Harbor

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.

Harmony Vineyards

Head of the Harbor Hotel Deals

Hyatt Regency Long Island

Hyatt Regency Long Island

4 out of 5
1717 Motor Parkway, Hauppauge, NY
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Nov 23 to Nov 24
$154 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,048 reviews)
Room ok. Other N/A

Reviewed on Oct 27, 2025

Hyatt Regency Long Island
Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 out of 5
2050 Express Dr S, Hauppauge, NY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Nov 6 to Nov 7
$136 total
Nov 6 - Nov 7
Total with taxes and fees
8/10 Very Good! (1,181 reviews)
Very good.

Reviewed on Oct 23, 2025

Holiday Inn Express Hauppauge-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
$92 nightly
The price is $105 total per night from Nov 2 to Nov 3
$105 total
Nov 2 - Nov 3
Total with taxes and fees
6.6/10 (1,383 reviews)
Staff is very nice and helpful. Rooms are pretty clean but are in need of severe updating. Ripped rugs, ripped wallpaper, sagging beds but comfortable. Breakfast could have more of a variety but overall good.

Reviewed on Oct 27, 2025

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
See all 1,130 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.

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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Frequently asked questions

How much does a Head of the Harbor vacation package cost?
You can grab a vacation package to this destination from $266 on Expedia. However, how much your vacation to Head of the Harbor costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Head of the Harbor?
You can typically find lower rates and better availability in December, January and February. Browse our cheap Head of the Harbor vacation packages and you could land some great off-season deals.
How many days is enough for Head of the Harbor?
The ideal length for your Head of the Harbor vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to check out all the top attractions and explore some hidden treasures along the way.
How to find the best Head of the Harbor package deals?
Finding a cheap Head of the Harbor 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 Harbor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Head of the Harbor vacation as a package?
Expedia vacation 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 customized Head of the Harbor vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Head of the Harbor?
If you're planning a spur-of-the-moment Head of the Harbor 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.
Does Expedia offer Book Now, Pay Later Head of the Harbor vacation packages?
Jet off on your perfect trip to Head of the Harbor with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.