Deals on vacations and trips to Head of the Harbor

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Head of the Harbor flight + hotel vacation packages

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Jun 6 - Jun 9
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Jul 17 - Jul 21
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 27
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free WiFi. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.
RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jun 2 - Jun 5
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, express check-out, and dry cleaning are also on offer.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jun 13 - Jun 16
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Prices and availability subject to change. Additional terms may apply.

Top Head of the Harbor hotel deals

Hyatt Regency Long Island

Hyatt Regency Long Island

3.5 out of 5
1717 Motor Parkway, Hauppauge, NY
Free Cancellation
The price is $149 per night
$149
per night
Apr 25 - Apr 26
A golf course, 2 outdoor tennis courts, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
Pool
Free WiFi
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
Free Cancellation
Reserve now, pay when you stay
The price is $108 per night
$108
per night
Apr 28 - Apr 29
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a terrace, and a grocery/convenience store are also offered.
Pet friendly
Breakfast available
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy, Hauppauge, NY
Free Cancellation
The price is $110 per night
$110
per night
Apr 25 - Apr 26
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Breakfast available
Pool
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Free Cancellation
Reserve now, pay when you stay
The price is $109 per night
$109
per night
May 14 - May 15
A restaurant and an outdoor pool are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pet friendly
Breakfast included
SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

2.5 out of 5
7940 Jericho Tpke, Woodbury, NY
Free Cancellation
Reserve now, pay when you stay
The price is $107 per night
$107
per night
May 6 - May 7
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pet friendly
Breakfast included
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

2.5 out of 5
10 Aero Rd, Bohemia, NY
Free Cancellation
Reserve now, pay when you stay
The price is $96 per night
$96
per night
Apr 29 - Apr 30
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a gym on site, and a 24-hour front desk and express check-in are also provided.
Pet friendly
Breakfast included
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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.

Popular places to visit

Image for Harmony Vineyards

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
Image for Short Beach

Short Beach

Why not spend a lazy afternoon at Short Beach during your trip to Nissequogue?

Short Beach

Frequently asked questions

How much are vacation packages to Head of the Harbor?
Spoil yourself with a memorable travel experience in Head of the Harbor with a vacation package starting at just $612. Locking in tours, flights and hotels through Travelocity is simple. On top of that, our packages will leave you with more cash in your pocket for loads of fun times.
Where can I get the best vacation package deals for Head of the Harbor?
Landing the perfect package deal to Head of the Harbor is a cinch with Travelocity. With access to 400 air carriers and 1,000,000 properties all over the globe, you won’t be short of choice when it comes to picking your flights and hotels.
Why should I purchase my Head of the Harbor vacation bundle with Travelocity?
Because you’ll never wander on your own if you book through us, and we offer round-the-clock customer support and exceptional service to boot. Add to that our Price Match Guarantee and a massive range of experiences to select from. We’re here to help you jet off on the vacation of a lifetime.
Will I save money on my Head of the Harbor car rental if I combine it with a hotel or flight?
Combining your hotel, flight and car into a Head of the Harbor vacation package is the easiest way to score an amazing deal. Plus, having your own wheels gives you freedom to find your way to all those famous sights you’re hoping to check out. Sitting 45 mi away from Head of the Harbor, Times Square is one attraction that should have a place on your itinerary. Load up the car and make a day trip of it.
What is the best time of year to go to Head of the Harbor?
May, June and July are the months when most people visit, while December, January and February are typically quieter. If your budget is limited, you’re better off visiting during . is typically the most expensive time of the year to come here.
Which airport is best for Head of the Harbor?
John F. Kennedy Intl. Airport (JFK), around 35 mi southwest of central Head of the Harbor, is most likely where you’ll jet into. Your other choices are Liberty Intl. Airport (EWR) (55 mi away from central Head of the Harbor) and LaGuardia Airport (LGA) (40 mi away from central Head of the Harbor).
What is there to do in Head of the Harbor?
Avalon Park and Preserve should be on your must-see list. Once you’ve crossed off this renowned attraction, simply stroll the streets of Head of the Harbor and experience what makes this cool destination tick.