Head of the Harbor Vacations from $283

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $600, price is now $283 per person
$283
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
It was a nice hotel. The bathroom was a little outdated and could have been a little cleaner.

Reviewed on Dec 14, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $806, price is now $340 per person
$340
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Staff was very kind and helpful. Rooms were very clean. The hotel was in a great location.

Reviewed on Dec 13, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,402, price is now $681 per person
$681
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Place was big, clean and well located

Reviewed on Dec 13, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $854, price is now $433 per person
$433
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Electric charging in back

Reviewed on Dec 9, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $818, price is now $417 per person
$417
per person
Mar 8 - Mar 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Room was clean. Staff was friendly. Hotel close to where we wanted to go.

Reviewed on Dec 14, 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

The Bella Vista St James! Waterfront house with a beach dock and so much more!

The Bella Vista St James! Waterfront house with a beach dock and so much more!

Saint James NY
$1,762 nightly
The price is $2,014 total per night from Dec 18 to Dec 19
$2,014 total
Dec 18 - Dec 19
Total with taxes and fees
10/10 Exceptional! (1 review)
This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to ...

Reviewed on Aug 10, 2025

The Bella Vista St James! Waterfront house with a beach dock and so much more!
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 Dec 21 to Dec 22
$154 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (1,084 reviews)
Glad to come back this year again!

Reviewed on Dec 13, 2025

Hyatt Regency Long Island
Days Inn by Wyndham Woodbury Long Island

Days Inn by Wyndham Woodbury Long Island

2.5 out of 5
8030 Jericho Tpke Woodbury NY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $105 total per night from Dec 17 to Dec 18
$105 total
Dec 17 - Dec 18
Total with taxes and fees
7.2/10 Good! (1,005 reviews)
Clean and comfy

Reviewed on Dec 7, 2025

Days Inn by Wyndham Woodbury Long Island
See all 1,100 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 $283 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.