A coastal town with a marina filled with boats, a lighthouse, and a hill with buildings.

Find hotels in Head of the Harbor, NY from CA $116

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Sep 3 - Sep 4
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Sep 4 - Sep 5
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Sep 4 - Sep 6
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Sep 11 - Sep 13

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Our top choices for Head of the Harbor hotels

1. Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG
Centereach
United States
Wade
CA $159
CA $181 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Stony Brook by IHG

2. Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook
Stony Brook
United States
Matthew
CA $211
CA $241 total
includes taxes & fees
Sep 14 - Sep 15
Hilton Garden Inn Stony Brook

3. Hampton Inn Long Island/Islandia

Hampton Inn Long Island/Islandia
Islandia
United States
Daniel
CA $186
CA $212 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn Long Island/Islandia

4. Hyatt Regency Long Island

Hyatt Regency Long Island
Hauppauge
United States
Lisa
CA $199
CA $227 total
includes taxes & fees
Oct 4 - Oct 5
Hyatt Regency Long Island

5. Holiday Inn Long Island-Islip Arpt East by IHG

Holiday Inn Long Island-Islip Arpt East by IHG
Holtsville
United States
Nicholas
CA $163
CA $187 total
includes taxes & fees
Sep 9 - Sep 10
Holiday Inn Long Island-Islip Arpt East by IHG

6. Courtyard by Marriott Long Island MacArthur Airport

Courtyard by Marriott Long Island MacArthur Airport
Ronkonkoma
United States
MD Ekrim
CA $220
CA $251 total
includes taxes & fees
Sep 13 - Sep 14
Courtyard by Marriott Long Island MacArthur Airport

7. Residence Inn by Marriott Long Island Holtsville

Residence Inn by Marriott Long Island Holtsville
Holtsville
United States
Tara
CA $187
CA $214 total
includes taxes & fees
Sep 7 - Sep 8
Residence Inn by Marriott Long Island Holtsville

8. Danfords Hotel and Marina

Danfords Hotel and Marina
Port Jefferson
United States
Alexander
CA $199
CA $280 total
includes taxes & fees
Sep 7 - Sep 8
Danfords Hotel and Marina

9. Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only
Islandia
United States
WILLIAM
CA $169
CA $193 total
includes taxes & fees
Sep 8 - Sep 9
Jake's 58 Casino Hotel - Adult Only

10. La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Bohemia
United States
MICHELE
CA $130
CA $148 total
includes taxes & fees
Oct 4 - Oct 5
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

11. Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island
Hauppauge
United States
emmanuel
CA $192
CA $219 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Hauppauge-Long Island

12. Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport
Ronkonkoma
United States
Michael
CA $169
CA $193 total
includes taxes & fees
Sep 27 - Sep 28
Hilton Garden Inn Islip/MacArthur Airport

13. Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven
Farmingville
United States
Randall
CA $163
CA $187 total
includes taxes & fees
Sep 16 - Sep 17
Hampton Inn Long Island-Brookhaven

14. Residence Inn By Marriott Long Island Hauppauge

Residence Inn By Marriott Long Island Hauppauge
Hauppauge
United States
Debra
CA $210
CA $245 total
includes taxes & fees
Sep 28 - Sep 29
Residence Inn By Marriott Long Island Hauppauge

15. Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island
Medford
United States
Carl
CA $173
CA $198 total
includes taxes & fees
Sep 9 - Sep 10
Fairfield Inn by Marriott Medford Long Island

16. Homewood Suites by Hilton Ronkonkoma

Homewood Suites by Hilton Ronkonkoma
Ronkonkoma
United States
Lisa
CA $215
CA $245 total
includes taxes & fees
Sep 27 - Sep 28
Homewood Suites by Hilton Ronkonkoma

17. Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island
Hauppauge
United States
Qiong
CA $164
CA $187 total
includes taxes & fees
Sep 14 - Sep 15
Radisson Hotel Hauppauge-Long Island

18. Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport
Ronkonkoma
United States
Paula
CA $101
CA $116 total
includes taxes & fees
Sep 20 - Sep 21
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

19. Residence Inn Long Island Islip/Courthouse Complex

Residence Inn Long Island Islip/Courthouse Complex
Central Islip
United States
Charlene
CA $206
CA $235 total
includes taxes & fees
Sep 7 - Sep 8
Residence Inn Long Island Islip/Courthouse Complex

20. Courtyard by Marriott Long Island Islip/Courthouse Complex

Courtyard by Marriott Long Island Islip/Courthouse Complex
Central Islip
United States
brandy
CA $199
CA $228 total
includes taxes & fees
Sep 8 - Sep 9
Courtyard by Marriott Long Island Islip/Courthouse Complex
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Stay near popular Head of the Harbor attractions

A coastal town with a marina filled with boats, a lighthouse, and a hill with buildings.

Avalon Park and Preserve

8.6/10 (4 reviews)
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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A wooden fence, a pond, and a house with white shutters.

Stony Brook Grist Mill

9.0/10 (7 reviews)
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.
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Harmony Vineyards

10.0/10 (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.
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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
A coastal town with a marina filled with boats, a lighthouse, and a hill with buildings.

Top Head of the Harbor Hotel Reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

8/10 Good
"Rooms were clean and tidy but a little dated Breakfast was ok for contimental Staff were great"
Stephen 2-night trip
Posted 1 hour ago
The Circle Hotel Fairfield
Grove Hotel

Grove Hotel

10/10 Excellent
"Another stay, another reminder why I keep coming back! ❤️ I’ve been staying at this hotel for years, many times every season, and somehow it still feels like coming home. The location, the atmosphere, the people and the energy of Cherry Grove make every stay special. This time was just as wonderful as always. Everything was comfortable, welcoming and exactly what I needed. There’s something about this place that keeps bringing me back again and again — and honestly, I wouldn’t want it any other way. Thank you for another amazing stay! See you again very soon… because you already know I’ll be back! 😉❤️"
Piotr 1-night trip
Posted 4 hours ago
Grove Hotel
Holiday Inn Plainview-Long Island by IHG

Holiday Inn Plainview-Long Island by IHG

10/10 Excellent
"I really enjoyed the massive coffee marked in the lobby area and breakfast was great me and my family enjoyed the weekend here!"
Krystyn 2-night trip
Posted 10 hours ago
Holiday Inn Plainview-Long Island by IHG
Courtyard by Marriott Long Island Islip/Courthouse Complex

Courtyard by Marriott Long Island Islip/Courthouse Complex

10/10 Excellent
"Muy limpio todo la recepcionista muy amable todo"
Iris 1-night trip
Posted 2 days ago
Courtyard by Marriott Long Island Islip/Courthouse Complex
Marriott Melville Long Island

Marriott Melville Long Island

8/10 Good
"Front desk staff were very friendly. Bed was very comfy."
Valerie 1-night trip
Posted 2 days ago
Marriott Melville Long Island
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

10/10 Excellent
"I thanks everyone for theirs kindness. You are amazing. 👏👏👏👏👏"
Janet 5-night trip
Posted 3 days ago
Radisson Hotel Hauppauge-Long Island

More cheap stays in Head of the Harbor

SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

7940 Jericho Tpke Woodbury NY
CA $130
CA $145 total
Sep 7 - Sep 8
includes taxes & fees
7.4/10 Good! (1,006 reviews)
SureStay Plus by Best Western Woodbury Inn
Comfort Inn Medford - Long Island

Comfort Inn Medford - Long Island

2695 Route 112 Medford NY
CA $157
CA $180 total
Sep 29 - Sep 30
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
Comfort Inn Medford - Long Island
Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG

3131 Nesconset Hwy Centereach NY
CA $159
CA $181 total
Sep 13 - Sep 14
includes taxes & fees
Holiday Inn Express Stony Brook by IHG
Days Inn by Wyndham Woodbury Long Island

Days Inn by Wyndham Woodbury Long Island

8030 Jericho Tpke Woodbury NY
CA $172
CA $192 total
Oct 2 - Oct 3
includes taxes & fees
Days Inn by Wyndham Woodbury Long Island
Extended Stay America Suites Long Island Melville

Extended Stay America Suites Long Island Melville

100 Spagnoli Rd Melville NY
CA $181
CA $206 total
Sep 7 - Sep 8
includes taxes & fees
Extended Stay America Suites Long Island Melville
 Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY
CA $192
CA $219 total
Sep 7 - Sep 8
includes taxes & fees
Holiday Inn Express Hauppauge-Long Island

Hotels in Head of the Harbor with star rating

Frequently asked questions

What is the best area to stay in Head Of The Harbor?
The best area to stay in Head Of The Harbor is along the scenic North Shore, particularly around the waterfront properties near Stony Brook and Port Jefferson.This area is characterised by its picturesque coastal views, charming villages, and access to outdoor activities. It's known for its beautiful homes, tree-lined streets, and proximity to various coves and harbours. The main roads like Route 25A connect these villages, offering easy access to local shops and eateries.For couples seeking a refined and relaxed getaway, staying in this region offers a wonderful experience. You can enjoy strolls along the water, visit local vineyards, or explore the quaint shops and art galleries in villages like Stony Brook. The area provides a tranquil setting great for unwinding.Families will also find this area appealing due to its access to nature and family-friendly attractions. Nearby parks and beaches offer opportunities for outdoor fun, and some accommodations provide amenities like swimming pools and spacious grounds.
When is the best time to go to Head Of The Harbor?
The best time to go to Head Of The Harbor is during the late spring (May to early June) and early autumn (September to October) months. These periods offer pleasant weather, ideal for exploring the area without the peak summer crowds.During late spring, the temperatures are mild, and the natural landscape is in full bloom, making it great for outdoor activities like walking along the harbour or visiting local gardens. You'll find fewer visitors at popular spots, allowing for a more relaxed experience.Early autumn provides similarly comfortable temperatures and beautifully changing foliage, particularly appealing for scenic drives and enjoying the local produce at farm stands.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Head of the Harbor.
How much is the nightly rate at a Head of the Harbor hotel?
Prices for hotels in Head of the Harbor often vary, but you can find a great deal from CA $116 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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