Book Hotels in Head of the Harbor, NY

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Top Head of the Harbor hotels

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road Fairfield CT
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $134 total per night from Dec 1 to Dec 2
$134 total
Dec 1 - Dec 2
Total with taxes and fees
A restaurant and a seasonal outdoor pool are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate ...
The rooms were clean and hotel is quiet . Breakfast was fine and staff was friendly.

Reviewed on Nov 17, 2025

Opens in a new windowThe Circle Hotel Fairfield
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
$103 nightly
The price is $118 total per night from Nov 30 to Dec 1
$118 total
Nov 30 - Dec 1
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 ...
The room was clean for the price. My only issue is that the cleaning lady came to my door to tell me it was time to check out wish made me rush as I was going to a wedding and needed time to get ready. But the beautiful gentleman in the reception desk help by giving me 1:30 hour more. Breakfast was ...

Reviewed on Nov 11, 2025

Opens in a new windowHampton Inn Long Island-Brookhaven
Marriott Melville Long Island

Marriott Melville Long Island

3.5 out of 5
1350 Walt Whitman Rd Melville NY
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $239 total per night from Dec 21 to Dec 22
$239 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet ...
Everything was great!!

Reviewed on Nov 8, 2025

Opens in a new windowMarriott Melville Long Island
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
$127 nightly
The price is $145 total per night from Dec 2 to Dec 3
$145 total
Dec 2 - Dec 3
Total with taxes and fees
A casino and a restaurant are featured at this smoke-free hotel. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking ...
Clean,staff friendly

Reviewed on Nov 13, 2025

Opens in a new windowJake's 58 Casino Hotel - Adult Only
 Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 out of 5
2050 Express Dr S Hauppauge NY
Fully refundable
$127 nightly
The price is $145 total per night from Dec 7 to Dec 8
$145 total
Dec 7 - Dec 8
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 ...
Great stay

Reviewed on Nov 14, 2025

Opens in a new window Holiday Inn Express Hauppauge-Long Island
Hyatt Regency Long Island

Hyatt Regency Long Island

4 out of 5
1717 Motor Parkway Hauppauge NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Nov 24 to Nov 25
$145 total
Nov 24 - Nov 25
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 ...
Room was great. Staff was great. Free parking. And awesome breakfast

Reviewed on Nov 14, 2025

Opens in a new windowHyatt 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
$99 nightly
The price is $111 total per night from Dec 21 to Dec 22
$111 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling for business? Take advantage of the 24-hour business center, ...
Room was clean, but a real negative not having a microwave in the rooms.

Reviewed on Nov 20, 2025

Opens in a new windowDays Inn by Wyndham Woodbury 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
$94 nightly
The price is $108 total per night from Nov 23 to Nov 24
$108 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take ...
Everything is always great

Reviewed on Nov 20, 2025

Opens in a new windowLa Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
$122 nightly
The price is $140 total per night from Nov 23 to Nov 24
$140 total
Nov 23 - Nov 24
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. ...
Excellent as always. Front staff friendly Reggie and the others. Housekeeping Kelly, Steven and room service Rosa. Thanks all of you guys for your service.

Reviewed on Nov 12, 2025

Opens in a new windowRadisson Hotel Hauppauge-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 $108. 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 1,107 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.

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