Head of the Harbor Vacations from $366

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $712, price is now $366 per person
$366
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
The hotel itself was nice. There is truly nothing but senior citizens that stay here. We walked in and thought it was a nursing home. I’m not joking there must have been at least 60 70year olds when we walked in. They just take over the entire hotel. Again, the hotel itself is nice, but I think we would stay somewhere else knowing what we know now especially with two teenage boys with us.

Reviewed on Aug 28, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,480, price is now $1,630 per person
$1,630
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,005 reviews)
Great hotel. Small rooms

Reviewed on Aug 31, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,404, price is now $1,302 per person
$1,302
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Everyone was helpful and super friendly.

Reviewed on Aug 28, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,754, price is now $974 per person
$974
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,303 reviews)
Solid Marriott but a few design issues-oddly our unit was noticeably underlighted with no ceiling light near door and closet and much too dim in-mirror lighting in bathroom. Also, oddly, no full length mirror in unit. But very clean unit with helpful staff and attractive dining and fitness level.

Reviewed on Sep 1, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,307, price is now $727 per person
$727
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (563 reviews)
Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound

Reviewed on Aug 18, 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

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
$144 nightly
The price is $164 total per night from Sep 14 to Sep 15
$164 total
Sep 14 - Sep 15
Total with taxes and fees
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
$98 nightly
The price is $112 total per night from Oct 2 to Oct 3
$112 total
Oct 2 - Oct 3
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $125 total per night from Sep 4 to Sep 5
$125 total
Sep 4 - Sep 5
Total with taxes and fees
Hampton Inn Long Island-Brookhaven
See all 1,082 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.

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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 $366 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.