Find hotels in Head of the Harbor, NY from ￥15,490

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Dec 12 - Dec 13
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Dec 13 - Dec 14
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Dec 12 - Dec 14
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Dec 19 - Dec 21

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Our top choices for Head of the Harbor hotels

Terrace/patio
Danfords Hotel and Marina

Danfords Hotel and Marina

Danfords Hotel and Marina
3.5 star property
Port Jefferson
8.4 out of 10, Very Good, (1001)
"Excellent, pleasant front desk service"
United States
William
The price is ￥23,650
￥32,175 total
includes taxes & fees
Dec 14 - Dec 15
Danfords Hotel and Marina
Free daily buffet breakfast
Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island
2.5 star property
Medford
8.8 out of 10, Excellent, (1002)
"always an excellent stay "
United States
tanya
The price is ￥18,066
￥20,641 total
includes taxes & fees
Dec 18 - Dec 19
Fairfield Inn by Marriott Medford Long Island
Panoramic Room | Memory foam beds, individually decorated, individually furnished
The Surfside Hotel

The Surfside Hotel

The Surfside Hotel
2.0 star property
Lordship
9.4 out of 10, Exceptional, (171)
"Great place to stay"
United States
Craig
The price is ￥20,184
￥23,212 total
includes taxes & fees
Dec 29 - Dec 30
The Surfside Hotel
Property amenity
Holiday Inn Long Island-Islip Arpt East by IHG

Holiday Inn Long Island-Islip Arpt East by IHG

Holiday Inn Long Island-Islip Arpt East by IHG
3.0 star property
Holtsville
9.2 out of 10, Wonderful, (844)
"Was nice place to stay after the first two hotels were so bad!!!!! "
United States
RONALD
The price is ￥15,730
￥17,973 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Holiday Inn Long Island-Islip Arpt East by IHG
Indoor pool
Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook
3.0 star property
Stony Brook
9.0 out of 10, Wonderful, (1002)
"Great visit"
United States
steven
The price is ￥17,318
￥19,786 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Stony Brook
Property amenity
Courtyard by Marriott Long Island Islip/Courthouse Complex

Courtyard by Marriott Long Island Islip/Courthouse Complex

Courtyard by Marriott Long Island Islip/Courthouse Complex
3.0 star property
Central Islip
8.8 out of 10, Excellent, (861)
"They stay was great! Clean definitely would stay again!"
United States
Jessica
The price is ￥22,391
￥25,582 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Long Island Islip/Courthouse Complex
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Hyatt Regency Long Island

Hyatt Regency Long Island

Hyatt Regency Long Island
4.0 star property
Hauppauge
8.2 out of 10, Very Good, (1082)
"Great place! "
United States
Carla Maeling
The price is ￥21,015
￥24,009 total
includes taxes & fees
Dec 14 - Dec 15
Hyatt Regency Long Island
Free daily buffet breakfast
Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG
2.5 star property
Centereach
9.0 out of 10, Wonderful, (1004)
"The breakfast had a wide variety of choices. "
United States
Anthony
The price is ￥20,525
￥23,450 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Stony Brook by IHG
Terrace/patio
Chalet Inn & Suites Centerport

Chalet Inn & Suites Centerport

Chalet Inn & Suites Centerport
2.0 star property
Centerport
7.8 out of 10, Good, (760)
"A friendly staff and very good location in centerport"
United States
Virna
Chalet Inn & Suites Centerport
Property grounds
Oheka Castle Hotel & Estate

Oheka Castle Hotel & Estate

Oheka Castle Hotel & Estate
3.5 star property
Huntington
9.0 out of 10, Wonderful, (649)
"Clean room , pleasant staff and a beautiful location "
United States
Prof. Sasa
The price is ￥65,597
￥74,945 total
includes taxes & fees
Dec 15 - Dec 16
Oheka Castle Hotel & Estate
Indoor pool
Residence Inn by Marriott Long Island Holtsville

Residence Inn by Marriott Long Island Holtsville

Residence Inn by Marriott Long Island Holtsville
3.0 star property
Holtsville
8.8 out of 10, Excellent, (1001)
"Staff was very friendly and the room was a great size!"
United States
Niccole
The price is ￥21,014
￥24,008 total
includes taxes & fees
Dec 14 - Dec 15
Residence Inn by Marriott Long Island Holtsville
Terrace/patio
Hampton Inn & Suites Huntington Downtown

Hampton Inn & Suites Huntington Downtown

Hampton Inn & Suites Huntington Downtown
2.5 star property
Huntington
9.0 out of 10, Wonderful, (404)
"Room was perfect and spotless, best continental breakfast ever huge variety!"
United States
Jane
The price is ￥24,256
￥27,714 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Huntington Downtown
Exterior
Delamar Southport

Delamar Southport

Delamar Southport
4.0 star property
Southport
9.4 out of 10, Exceptional, (442)
"Excellent hotel. "
United States
Victoria
The price is ￥35,118
￥42,718 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Delamar Southport
Sauna, steam room, body treatments, hydrotherapy, aromatherapy
The Inn And Spa At East Wind

The Inn And Spa At East Wind

The Inn And Spa At East Wind
3.5 star property
Calverton
8.8 out of 10, Excellent, (878)
"It a beautiful facility, great guest services "
United States
Terry
The price is ￥17,313
￥19,779 total
includes taxes & fees
Dec 17 - Dec 18
The Inn And Spa At East Wind
Terrace/patio
Hilton Garden Inn Melville

Hilton Garden Inn Melville

Hilton Garden Inn Melville
3.0 star property
Plainview
8.8 out of 10, Excellent, (1005)
"Great stay , I enjoyed it "
United States
Jean
The price is ￥23,510
￥26,861 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Melville
Studio Suite, 1 King Bed, Kitchenette | Premium bedding, desk, laptop workspace, iron/ironing board
The Circle Hotel Fairfield

The Circle Hotel Fairfield

The Circle Hotel Fairfield
3.0 star property
Grasmere
9.0 out of 10, Wonderful, (1419)
"Clean, updated room, easy check in & out. Staff was very nice"
United States
cynthia
The price is ￥20,851
￥24,873 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Circle Hotel Fairfield
Terrace/patio
SpringHill Suites by Marriott Long Island Brookhaven

SpringHill Suites by Marriott Long Island Brookhaven

SpringHill Suites by Marriott Long Island Brookhaven
3.0 star property
North Bellport
8.4 out of 10, Very Good, (1000)
"Great staff, and the room was spacious! Loved my stay "
United States
Yessica Arely
The price is ￥17,726
￥20,251 total
includes taxes & fees
Dec 23 - Dec 24
SpringHill Suites by Marriott Long Island Brookhaven
Indoor pool, open 5:30 AM to 11:00 PM, sun loungers
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven
2.5 star property
Farmingville
8.8 out of 10, Excellent, (1248)
"The staff is great. The breakfast is good. The rooms are comfortable. "
United States
Kenyata
The price is ￥16,046
￥18,333 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hampton Inn Long Island-Brookhaven
Lobby
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel
2.5 star property
Grasmere
8.0 out of 10, Very Good, (1000)
"Very nice clean room and easy parking. "
United States
Joe
The price is ￥23,166
￥26,641 total
includes taxes & fees
Dec 14 - Dec 15
Best Western Plus Fairfield Hotel
Reception
Come As You Are Inn

Come As You Are Inn

Come As You Are Inn
3.0 star property
Sayville
10.0 out of 10, Exceptional, (58)
"Nice breakfast"
United States
Jose
The price is ￥34,986
￥39,973 total
includes taxes & fees
Dec 13 - Dec 14
Come As You Are Inn
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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Stay near popular Head of the Harbor attractions

Avalon Harbor Aerial view from the hills - Catalina Island, California

Avalon Park and Preserve

Explore the great outdoors at Avalon Park and Preserve, a lovely green space in Head of the Harbor. Attend a sporting event in this family-friendly area.
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Reflections in stream and flowers in bloom at Stony Brook Grist Mill.; Brewster, Massachusetts.

Stony Brook Grist Mill

Find out about the history of Head of the Harbor when you take a trip to Stony Brook Grist Mill. While you're in the area, wander around the parks.
See properties

Learn more about Head of the Harbor

Head of the Harbor awaits: its wineries, parks, and more!

See all hotels in Head of the Harbor
Avalon Harbor Aerial view from the hills - Catalina Island, California

Top Head of the Harbor Hotel Reviews

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

10/10 Excellent
"Good"
Ikromjon 1-night trip
Posted 17 hours ago
Holiday Inn Express Hauppauge-Long Island

More cheap stays in Head of the Harbor

Hampton Inn Long Island/Islandia

Hampton Inn Long Island/Islandia

1600 Veterans Memorial Hwy Islandia NY
The price is ￥13,558 per night from Dec 21 to Dec 22
￥13,558
￥15,490 total
Dec 21 - Dec 22
includes taxes & fees
8.4/10 Very Good! (1,043 reviews)

Frequently asked questions

What's the best place for a stay in Head of the Harbor?
Hyatt Regency Long Island, located 6.3 mi (10.1 km) from the heart of Head of the Harbor, is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Days Inn by Wyndham Woodbury Long Island and Holiday Inn Express Hauppauge-Long Island. See all available top hotels, or vacation rentals in Head of the Harbor.
What are some of the best vacation rentals that Head of the Harbor has to offer?
The Bella Vista St James! Waterfront house with a beach dock and so much more!: Visitors give good reviews to this Head of the Harbor vacation home rental, which is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub. See all vacation rentals in Head of the Harbor.
If I need to cancel my hotel reservation in Head of the Harbor, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Head of the Harbor.
Where can I learn more about changing or cancelling my trip to Head of the Harbor?
For additional details about rescheduling or cancelling your trip to Head of the Harbor, click here.
What is staying in Head of the Harbor like?
Visitors can enjoy all that Head of the Harbor has to offer including the wineries and parks. There are 1106 hotels and other accommodations in the surrounding area. Find out more about Head of the Harbor.
What should I do while I'm visiting Head of the Harbor?
Favorite places to visit include Avalon Park and Preserve, Stony Brook Grist Mill, and Harmony Vineyards. You'll also find Long Island Museum of American Art, History, and Carriages and Smithaven Mall in the area. Check out what more to see and do in Expedia's Head of the Harbor guide.
What's the weather like in Head of the Harbor?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Head of the Harbor is 55 inches.

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