Find hotels in Head of the Harbor, NY from ￥14,977

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Dec 3 - Dec 4
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Dec 4 - Dec 5
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Dec 5 - Dec 7
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Dec 12 - Dec 14

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Compare 1,113 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

BBQ/picnic area
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)
"Great stay."
United States
Angela
The price is ￥21,024
￥24,019 total
includes taxes & fees
Dec 18 - Dec 19
Residence Inn by Marriott Long Island Holtsville
Exterior
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

3.0 star property
Bohemia
6.8 out of 10, (1430)
"Great stay, no problems."
United States
Wayne
The price is ￥14,669
￥16,760 total
includes taxes & fees
Dec 18 - Dec 19
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Lobby
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, (838)
"The staff made the stay simple and pleasant. "
United States
Osvaldo
The price is ￥16,054
￥18,341 total
includes taxes & fees
Dec 18 - Dec 19
Holiday Inn Long Island-Islip Arpt East by IHG
Gazebo
Quality Suites Stratford

Quality Suites Stratford

2.5 star property
Stratford
8.0 out of 10, Very Good, (1000)
"It was quite and very clean great customer service "
United States
Angelina
The price is ￥14,710
￥16,916 total
includes taxes & fees
Dec 21 - Dec 22
Quality Suites Stratford
Breakfast served, American cuisine
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 star property
Hauppauge
6.4 out of 10, (1298)
"Amazing Will stay again"
United States
Luis
The price is ￥17,718
￥20,243 total
includes taxes & fees
Dec 16 - Dec 17
Radisson Hotel Hauppauge-Long Island
Exterior
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (1422)
"Nice hotel in Fairfield, Ct"
United States
Veronica
The price is ￥17,314
￥20,806 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Circle Hotel Fairfield
Exterior
Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 star property
Hauppauge
8.2 out of 10, Very Good, (1243)
"Great stay"
United States
Maria
The price is ￥19,814
￥22,637 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Hauppauge-Long Island
Lobby
Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport

3.0 star property
Ronkonkoma
8.4 out of 10, Very Good, (1014)
"Ellen was very pleasant and quick check in "
United States
Anthony
The price is ￥17,298
￥19,762 total
includes taxes & fees
Dec 18 - Dec 19
Hilton Garden Inn Islip/MacArthur Airport
Exterior
Delamar Southport

Delamar Southport

4.0 star property
Southport
9.4 out of 10, Exceptional, (440)
"Excellent hotel. "
United States
Victoria
The price is ￥41,014
￥49,499 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Delamar Southport
Exterior
Courtyard by Marriott Long Island MacArthur Airport

Courtyard by Marriott Long Island MacArthur Airport

3.0 star property
Ronkonkoma
8.6 out of 10, Excellent, (1003)
"The front desk crew were great and helpful"
United States
Hector
The price is ￥18,543
￥21,185 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Courtyard by Marriott Long Island MacArthur Airport
Restaurant
Clarion Hotel & Conference Center

Clarion Hotel & Conference Center

3.0 star property
Ronkonkoma
5.0 out of 10, (1001)
"Good stay"
United States
Jorge
The price is ￥14,502
￥16,568 total
includes taxes & fees
Dec 7 - Dec 8
Clarion Hotel & Conference Center
Daily cooked-to-order breakfast (USD 11.00 per person)
Hyatt Regency Long Island

Hyatt Regency Long Island

4.0 star property
Hauppauge
8.2 out of 10, Very Good, (1089)
"Nice rooms beautiful lobby. "
United States
Michael
The price is ￥21,024
￥24,018 total
includes taxes & fees
Dec 18 - Dec 19
Hyatt Regency Long Island
Lobby
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 star property
Fairfield
8.0 out of 10, Very Good, (1000)
"Very nice clean room and easy parking. "
United States
Joe
The price is ￥23,177
￥26,654 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Plus Fairfield Hotel
Panoramic Room | Memory foam beds, individually decorated, individually furnished
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 ￥20,399
￥23,459 total
includes taxes & fees
Dec 9 - Dec 10
The Surfside Hotel
2 Double Beds Non-Smoking | Premium bedding, blackout drapes, iron/ironing board, free WiFi
Hampton Inn Long Island/Islandia

Hampton Inn Long Island/Islandia

2.5 star property
Islandia
8.6 out of 10, Excellent, (1042)
"Great hotel"
United States
Kenneth
The price is ￥13,583
￥15,518 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn Long Island/Islandia
Lobby
Residence Inn by Marriott Norwalk

Residence Inn by Marriott Norwalk

3.0 star property
Norwalk
8.8 out of 10, Excellent, (347)
"Great property"
United States
Karl
The price is ￥26,313
￥30,260 total
includes taxes & fees
Dec 18 - Dec 19
Residence Inn by Marriott Norwalk
Free daily buffet breakfast
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, (1000)
"Clean room, good breakfast, quiet, helpful staff"
United States
Brenda
The price is ￥20,534
￥23,460 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Stony Brook by IHG
Terrace/patio
Hilton Garden Inn Melville

Hilton Garden Inn Melville

3.0 star property
Plainview
8.8 out of 10, Excellent, (1001)
"Great stay , I enjoyed it "
United States
Jean
The price is ￥22,276
￥25,451 total
includes taxes & fees
Dec 29 - Dec 30
Hilton Garden Inn Melville
Free cribs/infant beds, rollaway beds, free WiFi, bed sheets
Rodeway Inn Macarthur Airport

Rodeway Inn Macarthur Airport

2.0 star property
Ronkonkoma
6.8 out of 10, (1000)
"Was such a nice stay with the best staff all summer"
United States
Noelle
The price is ￥13,108
￥14,977 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Rodeway Inn Macarthur Airport
Exterior detail
Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

3.5 star property
Islandia
8.2 out of 10, Very Good, (1297)
"Very clean room and professional staff!"
United States
Latoya
The price is ￥17,756
￥20,287 total
includes taxes & fees
Dec 11 - Dec 12
Jake's 58 Casino Hotel - Adult Only
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

Hyatt Regency Long Island

Hyatt Regency Long Island

10/10 Excellent
"The room was perfect. Staff were beyond wonderful, especially Elizabeth at the front desk"
Joseph 1-night trip
Posted 2 days ago
Hyatt Regency Long Island

More cheap stays in Head of the Harbor

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY
The price is ￥19,814 per night from Dec 14 to Dec 15
￥19,814
￥22,637 total
Dec 14 - Dec 15
includes taxes & fees
8/10 Very Good! (1,240 reviews)

Frequently asked questions

What's the best place for a stay in Head of the Harbor?
Radisson Hotel Hauppauge-Long Island, located 8.7 mi (14 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 Hyatt Regency Long Island and La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport. 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?
Business or Weekend escape: This vacation home rental near Head of the Harbor offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker. 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 1111 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 Smithaven Mall and Sunken Meadow State Park 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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