Head of the Harbor Holiday Rentals, St. James: Private House Rentals

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Go beyond your typical stay in Head of the Harbor

Pet friendly

Apartment

Pool

Condo

Spa

Hot tub

Cottage

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Head of the Harbor hotels

1. Holiday Inn Express Stony Brook by IHG

Centereach

฿4,075

฿4,655 total

includes taxes & fees

20 Sept - 21 Sept

2. Hilton Garden Inn Stony Brook

Stony Brook

Kimberly

฿4,782

฿5,463 total

includes taxes & fees

5 Oct - 6 Oct

3. Hampton Inn Long Island-Brookhaven

Farmingville

Randall

฿4,058

฿4,636 total

includes taxes & fees

20 Sept - 21 Sept

4. Homewood Suites by Hilton Ronkonkoma

Ronkonkoma

Lisa

฿5,147

฿5,880 total

includes taxes & fees

27 Sept - 28 Sept

5. Residence Inn By Marriott Long Island Hauppauge

Hauppauge

Debra

฿5,060

฿5,897 total

includes taxes & fees

4 Oct - 5 Oct

6. Hyatt Regency Long Island

Hauppauge

Lisa

฿4,782

฿5,463 total

includes taxes & fees

4 Oct - 5 Oct

7. Courtyard by Marriott Long Island MacArthur Airport

Ronkonkoma

MD Ekrim

฿5,281

฿6,033 total

includes taxes & fees

17 Sept - 18 Sept

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

Holtsville

Nicholas

฿3,928

฿4,488 total

includes taxes & fees

4 Oct - 5 Oct

9. Residence Inn by Marriott Long Island Holtsville

Holtsville

Tara

฿4,488

฿5,128 total

includes taxes & fees

27 Sept - 28 Sept

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

Bohemia

Andrea

฿3,063

฿3,499 total

includes taxes & fees

5 Oct - 6 Oct

11. Holiday Inn Express Hauppauge-Long Island

Hauppauge

emmanuel

฿4,330

฿4,947 total

includes taxes & fees

20 Sept - 21 Sept

12. Radisson Hotel Hauppauge-Long Island

Hauppauge

Iwona

฿4,065

฿4,644 total

includes taxes & fees

28 Sept - 29 Sept

13. Hampton Inn Long Island/Islandia

Islandia

Viviana

฿4,134

฿4,724 total

includes taxes & fees

7 Oct - 8 Oct

14. Jake's 58 Casino Hotel - Adult Only

Islandia

WILLIAM

฿2,515

฿2,874 total

includes taxes & fees

28 Sept - 29 Sept

15. Danfords Hotel and Marina

Port Jefferson

Alexander

฿5,603

฿7,706 total

includes taxes & fees

15 Oct - 16 Oct

16. Hilton Garden Inn Islip/MacArthur Airport

Ronkonkoma

Elizabeth

฿3,933

฿4,494 total

includes taxes & fees

12 Oct - 13 Oct

17. Courtyard by Marriott Long Island Islip/Courthouse Complex

Central Islip

DAVID

฿4,782

฿5,464 total

includes taxes & fees

24 Sept - 25 Sept

18. Fairfield Inn by Marriott Medford Long Island

Medford

Carl

฿4,015

฿4,587 total

includes taxes & fees

5 Oct - 6 Oct

19. Residence Inn Long Island Islip/Courthouse Complex

Central Islip

Sareka

฿4,934

฿5,637 total

includes taxes & fees

21 Sept - 22 Sept

20. Comfort Inn Medford - Long Island

Medford

Daisy

฿3,544

฿4,049 total

includes taxes & fees

4 Oct - 5 Oct

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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 with a stop at 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

Top Head of the Harbor Hotel Reviews

Hampton Inn Long Island-Brookhaven

8/10 Good

"Modern hotel, well maintained. Large, heated indoor pool was good for relaxing or doing laps. Breakfast was good and always refilled. They charged us twice for parking fee ($15/night) but said they would reverse the duplicate charge (still haven't seen the credit on card though). Make sure you review your bill before leaving."

Hilton Garden Inn Melville

10/10 Excellent

"Room was spotless. The food for breakfast and evening was very good. The staff were Very personable."

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

10/10 Excellent

"Great location"

Hilton Long Island/Huntington

10/10 Excellent

"Room was well designed and bed very comfortable"

SureStay Plus by Best Western Woodbury Inn

8/10 Good

"They did not allow to keep my bag for a couple hours when early checkin was not available. This is bad customer service. Should allow bag claim team to keep the bag for claim once checkin is done a couple hours later"

Danfords Hotel and Marina

10/10 Excellent

"Love where is located. Very peaceful and calm"

The Circle Hotel Fairfield

10/10 Excellent

"Comfortable beds, quiet, very good breakfast"

Holiday Inn Express Stony Brook by IHG

8/10 Good

"Have to update the outlet for the new iPhones. All the chargers have the USB plug."

Holiday Inn Plainview-Long Island by IHG

8/10 Good

"great accomodations but the air conditionerwas noisey each time it shut off."

More cheap stays in Head of the Harbor

Comfort Inn Medford - Long Island

2695 Route 112 Medford NY

฿3,544

฿4,049 total

4 Oct - 5 Oct

includes taxes & fees

8.4/10 Very good! (1,010 reviews)

Extended Stay America Suites Long Island Melville

100 Spagnoli Rd Melville NY

฿4,044

฿4,621 total

17 Sept - 18 Sept

includes taxes & fees

SureStay Plus by Best Western Woodbury Inn

7940 Jericho Tpke Woodbury NY

฿4,155

฿4,638 total

28 Sept - 29 Sept

includes taxes & fees

7.4/10 Good! (1,007 reviews)

Holiday Inn Express Stony Brook by IHG

3131 Nesconset Hwy Centereach NY

฿4,075

฿4,655 total

20 Sept - 21 Sept

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

Days Inn by Wyndham Woodbury Long Island

8030 Jericho Tpke Woodbury NY

฿4,261

฿4,756 total

11 Oct - 12 Oct

includes taxes & fees

7.4/10 Good! (1,004 reviews)

Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY

฿4,330

฿4,947 total

20 Sept - 21 Sept

includes taxes & fees

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 traveller data. Other good options for your trip to the area are Holiday Inn Express Hauppauge-Long Island and Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport. See all available top hotels, or 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, you'll find most hotel reservations are refundable if you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Head of the Harbor.

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 1057 hotels and other accommodation options in the surrounding area. Find out more about Head of the Harbor.

What should I see while I'm in Head of the Harbor?

Favourite 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. Take a look at what more there is to see and do in Expedia's Head of the Harbor guide.

What's the seasonal weather in Head of the Harbor?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Head of the Harbor is 1400 mm.

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Find hotels in Head of the Harbor, NY from ฿2,874

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Head of the Harbor

Check prices for these dates

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Our top choices for Head of the Harbor hotels

1. Holiday Inn Express Stony Brook by IHG

2. Hilton Garden Inn Stony Brook

3. Hampton Inn Long Island-Brookhaven

4. Homewood Suites by Hilton Ronkonkoma

5. Residence Inn By Marriott Long Island Hauppauge

6. Hyatt Regency Long Island

7. Courtyard by Marriott Long Island MacArthur Airport

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

9. Residence Inn by Marriott Long Island Holtsville

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

11. Holiday Inn Express Hauppauge-Long Island

12. Radisson Hotel Hauppauge-Long Island

13. Hampton Inn Long Island/Islandia

14. Jake's 58 Casino Hotel - Adult Only

15. Danfords Hotel and Marina

16. Hilton Garden Inn Islip/MacArthur Airport

17. Courtyard by Marriott Long Island Islip/Courthouse Complex

18. Fairfield Inn by Marriott Medford Long Island

19. Residence Inn Long Island Islip/Courthouse Complex

20. Comfort Inn Medford - Long Island

Stay near popular Head of the Harbor attractions

Avalon Park and Preserve

Stony Brook Grist Mill

Harmony Vineyards

Learn more about Head of the Harbor

Top Head of the Harbor Hotel Reviews

Hampton Inn Long Island-Brookhaven

Hilton Garden Inn Melville

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Hilton Long Island/Huntington

SureStay Plus by Best Western Woodbury Inn

Danfords Hotel and Marina

The Circle Hotel Fairfield

Holiday Inn Express Stony Brook by IHG

Holiday Inn Plainview-Long Island by IHG

More cheap stays in Head of the Harbor

Comfort Inn Medford - Long Island

Extended Stay America Suites Long Island Melville

SureStay Plus by Best Western Woodbury Inn

Holiday Inn Express Stony Brook by IHG

Days Inn by Wyndham Woodbury Long Island

Holiday Inn Express Hauppauge-Long Island

Frequently asked questions

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