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 $120

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Filter by

Star rating

Guest rating

Our top choices for Head of the Harbor hotels

1. Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook
Stony Brook
United States
Kimberly
CA $187
CA $214 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Garden Inn Stony Brook

2. Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG
Centereach
United States
Wade
CA $159
CA $182 total
includes taxes & fees
Oct 13 - Oct 14
Holiday Inn Express Stony Brook by IHG

3. Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven
Farmingville
United States
Randall
CA $169
CA $194 total
includes taxes & fees
Sep 20 - Sep 21
Hampton Inn Long Island-Brookhaven

4. Hyatt Regency Long Island

Hyatt Regency Long Island
Hauppauge
United States
Lisa
CA $199
CA $228 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 $154
CA $176 total
includes taxes & fees
Oct 13 - Oct 14
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 $187
CA $214 total
includes taxes & fees
Oct 4 - Oct 5
Courtyard by Marriott Long Island MacArthur Airport

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

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Bohemia
United States
Raymond
CA $128
CA $146 total
includes taxes & fees
Sep 15 - Sep 16
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

8. Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only
Islandia
United States
WILLIAM
CA $105
CA $120 total
includes taxes & fees
Sep 28 - Sep 29
Jake's 58 Casino Hotel - Adult Only

9. 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 24 - Sep 25
Residence Inn by Marriott Long Island Holtsville

10. Homewood Suites by Hilton Ronkonkoma

Homewood Suites by Hilton Ronkonkoma
Ronkonkoma
United States
Lisa
CA $215
CA $246 total
includes taxes & fees
Sep 17 - Sep 18
Homewood Suites by Hilton Ronkonkoma

11. Hilton Garden Inn Islip/MacArthur Airport

Hilton Garden Inn Islip/MacArthur Airport
Ronkonkoma
United States
Elizabeth
CA $169
CA $194 total
includes taxes & fees
Sep 27 - Sep 28
Hilton Garden Inn Islip/MacArthur Airport

12. Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island
Hauppauge
United States
emmanuel
CA $181
CA $207 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Express Hauppauge-Long Island

13. Hampton Inn Long Island/Islandia

Hampton Inn Long Island/Islandia
Islandia
United States
Viviana
CA $171
CA $195 total
includes taxes & fees
Oct 7 - Oct 8
Hampton Inn Long Island/Islandia

14. Danfords Hotel and Marina

Danfords Hotel and Marina
Port Jefferson
United States
Alexander
CA $235
CA $322 total
includes taxes & fees
Sep 14 - Sep 15
Danfords Hotel and Marina

15. Residence Inn By Marriott Long Island Hauppauge

Residence Inn By Marriott Long Island Hauppauge
Hauppauge
United States
Debra
CA $211
CA $246 total
includes taxes & fees
Oct 4 - Oct 5
Residence Inn By Marriott Long Island Hauppauge

16. Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island
Medford
United States
Carl
CA $167
CA $191 total
includes taxes & fees
Oct 5 - Oct 6
Fairfield Inn by Marriott Medford Long Island

17. Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport
Ronkonkoma
United States
Paula
CA $99
CA $113 total
includes taxes & fees
Sep 20 - Sep 21
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

18. Courtyard by Marriott Long Island Islip/Courthouse Complex

Courtyard by Marriott Long Island Islip/Courthouse Complex
Central Islip
Canada
DAVID
CA $200
CA $228 total
includes taxes & fees
Sep 17 - Sep 18
Courtyard by Marriott Long Island Islip/Courthouse Complex

19. Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island
Hauppauge
United States
Qiong
CA $170
CA $194 total
includes taxes & fees
Sep 20 - Sep 21
Radisson Hotel Hauppauge-Long Island

20. Residence Inn Long Island Islip/Courthouse Complex

Residence Inn Long Island Islip/Courthouse Complex
Central Islip
United States
Sareka
CA $206
CA $235 total
includes taxes & fees
Sep 21 - Sep 22
Residence Inn Long Island Islip/Courthouse Complex
View all properties
Save an average of 15% on thousands of hotels when you're signed in

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.
See properties
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.
See properties

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.
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
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

10/10 Excellent
"Great experience and great to have breakfast available"
Julie 1-night trip
Posted 7 hours ago
The Circle Hotel Fairfield
Holiday Inn Express Stony Brook by IHG

Holiday Inn Express Stony Brook by IHG

10/10 Excellent
"When on Long Island I will continue to stay at this property."
Mark 3-night trip
Posted 8 hours ago
Holiday Inn Express Stony Brook by IHG
Hilton Long Island/Huntington

Hilton Long Island/Huntington

10/10 Excellent
"Great place to stay with many amenities. The restaurant, pool, hot tub and proximity to many other places in the area."
Giuseppe 1-night trip
Posted 8 hours ago
Hilton Long Island/Huntington
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

10/10 Excellent
"Easy check in process, very friendly front desk staff! Would stay again 100%"
Omwatti 1-night trip
Posted 8 hours ago
Hampton Inn Long Island-Brookhaven
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

10/10 Excellent
"Bbj"
Raymond 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

8/10 Good
"Overall ok"
sam 1-night trip
Posted 2 days ago
Radisson Hotel Hauppauge-Long Island

More cheap stays in Head of the Harbor

Comfort Inn Medford - Long Island

Comfort Inn Medford - Long Island

2695 Route 112 Medford NY
CA $148
CA $169 total
Oct 7 - Oct 8
includes taxes & fees
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 $182 total
Oct 13 - Oct 14
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
Holiday Inn Express Stony Brook by IHG
SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

7940 Jericho Tpke Woodbury NY
CA $172
CA $192 total
Sep 28 - Sep 29
includes taxes & fees
SureStay Plus by Best Western Woodbury Inn
Extended Stay America Suites Long Island Melville

Extended Stay America Suites Long Island Melville

100 Spagnoli Rd Melville NY
CA $169
CA $193 total
Sep 14 - Sep 15
includes taxes & fees
Extended Stay America Suites Long Island Melville
Days Inn by Wyndham Woodbury Long Island

Days Inn by Wyndham Woodbury Long Island

8030 Jericho Tpke Woodbury NY
CA $175
CA $195 total
Oct 12 - Oct 13
includes taxes & fees
Days Inn by Wyndham Woodbury Long Island
 Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY
CA $181
CA $207 total
Sep 14 - Sep 15
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 $120 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.

Explore a world of travel with Expedia