Book Hotels in Head of the Harbor, NY

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May 29 - May 31
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Jun 5 - Jun 7

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Top Head of the Harbor hotels

Holiday Inn Long Island-Islip Arpt East by IHG

Holiday Inn Long Island-Islip Arpt East by IHG

3 out of 5
1730 N Ocean Ave Holtsville NY
Fully refundable
$139 nightly
The price is $159 total per night from Jun 1 to Jun 2
$159 total
Jun 1 - Jun 2
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"Great stay"

Reviewed on May 28, 2026

Opens in a new windowHoliday Inn Long Island-Islip Arpt East by IHG
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road Fairfield CT
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $177 total per night from Jun 3 to Jun 4
$177 total
Jun 3 - Jun 4
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"This was the perfect little hotel to be close to an event at the Fairfield Theater Company. Clean, reasonably priced rooms, friendly staff, nice Continental breakfast."

Reviewed on May 28, 2026

Opens in a new windowThe Circle Hotel Fairfield
Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG

2.5 out of 5
3131 Nesconset Hwy Centereach NY
Fully refundable
$179 nightly
The price is $205 total per night from Jun 3 to Jun 4
$205 total
Jun 3 - Jun 4
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
"fuimos para la graducaion de nuestros hijos de la universidad de Stony Brook . otras veces nos hemos hospedado en el hotl que se encuentra en el campo de la Universidad, pero este horel esta mucho mejor, mas moderno, limpio y el desayuno muy bueno."

Reviewed on May 29, 2026

Opens in a new windowHoliday Inn Express Stony Brook by IHG
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

3.5 out of 5
2000 North Ocean Ave. Farmingville NY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $164 total per night from Jun 29 to Jun 30
$164 total
Jun 29 - Jun 30
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet ...
"Good service with our short visit in NY"

Reviewed on May 29, 2026

Opens in a new windowHampton Inn Long Island-Brookhaven
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
$144 nightly
The price is $164 total per night from Jun 1 to Jun 2
$164 total
Jun 1 - Jun 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
"Breakfast could have better options"

Reviewed on May 28, 2026

Opens in a new window Holiday Inn Express Hauppauge-Long Island
SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

2.5 out of 5
7940 Jericho Tpke Woodbury NY
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $160 total per night from Jun 1 to Jun 2
$160 total
Jun 1 - Jun 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express ...
"Simple clean room w refrig. Breakfast is a great ammenity"

Reviewed on May 28, 2026

Opens in a new windowSureStay Plus by Best Western Woodbury Inn
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
$158 nightly
The price is $181 total per night from Jun 4 to Jun 5
$181 total
Jun 4 - Jun 5
Total with taxes and fees
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. ...
"Everything was perfect, clean, neat and very comfy."

Reviewed on May 29, 2026

Opens in a new windowRadisson Hotel Hauppauge-Long Island
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Jun 7 to Jun 8
$104 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. ...
"The whole star was horrible, bugs in the room told, arguing with the front desks 3 times, was told don’t complain again or you will be asked to check out"

Reviewed on May 29, 2026

Opens in a new windowClarion Hotel & Conference Center Ronkonkoma MacArthur Airport
Hyatt Regency Long Island

Hyatt Regency Long Island

4 out of 5
1717 Motor Parkway Hauppauge NY
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $166 total per night from May 31 to Jun 1
$166 total
May 31 - Jun 1
Total with taxes and fees
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 ...
Opens in a new windowHyatt Regency Long Island
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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.

Frequently asked questions

What are the top kid-friendly hotels in Head of the Harbor?
Take some of the struggles out of traveling with kids by choosing a family-friendly Head of the Harbor hotel. From useful amenities to extra-helpful services, these properties come with perks that'll make your visit run smoothly: You'll be well looked after at Three Village Inn. It comes with a nearby beach, front desk services and a commitment to making families feel at home. Room for rent in safe house surrounded by nature w/ private beach 8 min away! is also a great choice. After a long day of exploring, come home to your comfortable room and amenities like pet-friendly facilities and internet access.
Where can I find cheap hotels in Head of the Harbor?
At Travelocity you'll find really nice hotels in Head of the Harbor at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Head of the Harbor rather than in Head of the Harbor. We may find you even better rates, too.
How do I find the best Head of the Harbor hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Head of the Harbor then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Head of the Harbor?
The cheapest hotel in Head of the Harbor is $104. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Head of the Harbor?
There are 1,081 hotels in Head of the Harbor on Travelocity.
What are the best hotels in Head of the Harbor?
Head of the Harbor has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Head of the Harbor for you!
When is the best time to visit Head of the Harbor?
If you want the joy of a fun-filled trip in peak season, visit Head of the Harbor during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Head of the Harbor?
Based on historic data is usually the cheapest month to visit Head of the Harbor. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Head of the Harbor?
There are multiple hotels in Head of the Harbor that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Head of the Harbor. We have plenty of kid-friendly hotels in Head of the Harbor to choose from on Travelocity!
Why book a hotel in Head of the Harbor through Travelocity?
Because we have the top hotels in Head of the Harbor! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Head of the Harbor on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Head of the Harbor hotel reviews by fellow wanderers

Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Everything was perfect, clean, neat and very comfy."
A verified traveler stayed at Radisson Hotel Hauppauge-Long Island
Radisson Hotel Hauppauge-Long Island

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