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

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Pet friendly

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Our top choices for Head of the Harbor hotels

Breakfast included

Hotel

Reserve now, pay later

Pool

Wi-Fi included

Tempur-Pedic beds, desk, blackout curtains

1. Americas Best Value Inn Port Jefferson Station Long Island

Port Jefferson Station

Seth

4.156.113 ₫

4.748.084 ₫ total

includes taxes & fees

31 Aug - 1 Sept

2. Hilton Garden Inn Stony Brook

Stony Brook

Matthew

3.541.606 ₫

4.046.284 ₫ total

includes taxes & fees

7 Sept - 8 Sept

In-room safe, desk, blackout curtains, iron/ironing board

3. Holiday Inn Express Stony Brook by IHG

Centereach

Joanne

4.061.775 ₫

4.640.578 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Desk, laptop workspace, iron/ironing board, free cots/infant beds

4. Courtyard by Marriott Long Island MacArthur Airport

Ronkonkoma

Michael

3.010.365 ₫

3.439.342 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Room, 1 King Bed, Accessible, Non Smoking (Roll-in Shower) | Living area | 32-inch LCD TV with satellite channels, TV, pay films

5. Hampton Inn Long Island / Commack

Commack

Sarah

4.166.595 ₫

4.760.662 ₫ total

includes taxes & fees

9 Aug - 10 Aug

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

Holtsville

Nicholas

3.092.190 ₫

3.532.826 ₫ total

includes taxes & fees

8 Sept - 9 Sept

7. Residence Inn by Marriott Long Island Holtsville

Holtsville

Jen

3.541.606 ₫

4.046.285 ₫ total

includes taxes & fees

25 Aug - 26 Aug

Room, 2 Queen Beds, Non Smoking | Premium bedding, pillow-top beds, desk, blackout curtains

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

Bohemia

JUstine

2.704.356 ₫

3.089.726 ₫ total

includes taxes & fees

3 Sept - 4 Sept

9. Homewood Suites by Hilton Ronkonkoma

Ronkonkoma

Jean Paul

4.168.691 ₫

4.762.731 ₫ total

includes taxes & fees

1 Sept - 2 Sept

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

10. Home2 Suites by Hilton Long Island Brookhaven

Yaphank

Mark

3.760.418 ₫

4.296.277 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Premium bedding, desk, laptop workspace, iron/ironing board

11. The Circle Hotel Fairfield

Grasmere

Kori

3.752.555 ₫

4.577.750 ₫ total

includes taxes & fees

8 Sept - 9 Sept

12. Hilton Garden Inn Islip/MacArthur Airport

Ronkonkoma

Joseph

3.541.606 ₫

4.046.284 ₫ total

includes taxes & fees

7 Sept - 8 Sept

In-room safe, desk, laptop workspace, blackout curtains

13. Holiday Inn Express Hauppauge-Long Island

Hauppauge

Suzanne

3.541.606 ₫

4.046.285 ₫ total

includes taxes & fees

7 Sept - 8 Sept

14. Courtyard by Marriott Long Island Islip/Courthouse Complex

Central Islip

Maria

3.773.520 ₫

4.311.247 ₫ total

includes taxes & fees

17 Aug - 18 Aug

Indoor pool, open 5:30 AM to 11:00 PM, pool loungers

Desk, blackout curtains, iron/ironing board, free cots/infant beds

15. Hampton Inn Long Island-Brookhaven

Farmingville

JOSE

3.201.703 ₫

3.657.940 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Room, 1 King Bed with Sofa bed, Non Smoking (Upgrade) | Desk, blackout curtains, iron/ironing board, free cots/infant beds

16. Comfort Inn Medford - Long Island

Medford

Steven

3.182.073 ₫

3.635.518 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Basic Studio Suite | Iron/ironing board, free WiFi, bed sheets

17. Jake's 58 Casino Hotel - Adult Only

Islandia

WILLIAM

3.704.601 ₫

4.232.370 ₫ total

includes taxes & fees

9 Aug - 10 Aug

18. Danfords Hotel and Marina

Port Jefferson

Marcela

4.589.020 ₫

6.276.595 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Premium bedding, down duvets, desk, laptop workspace

19. Fairfield Inn by Marriott Medford Long Island

Medford

Vishnu

3.160.323 ₫

3.610.668 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Suite, Multiple Beds, Non Smoking | Premium bedding, desk, free cots/infant beds, free WiFi

20. Quality Suites Stratford

Stratford

Andrew

2.722.962 ₫

3.131.406 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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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

Best Western Premier Plainview-Long Island Hotel

8/10 Good

"Nice, clean hotel. Staff were friendly and efficient."

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

8/10 Good

"The hotel is slowly being remodeled, not every room or floor has been redone, that said not a bad place for the price. Friendly and helpful staff."

The Circle Hotel Fairfield

8/10 Good

"Nice place to stay while visiting Fairfield. The room was clean and comfortable. The pool could have been cleaner and I wish there had been a vent fan in the bathroom because the room seemed a little humid."

Hampton Inn Long Island-Brookhaven

10/10 Excellent

"Very nice staff. Breakfast was great! My room was an icebox and it was perfect. The beds are very comfy!!"

SureStay Plus by Best Western Woodbury Inn

10/10 Excellent

"Excellent!"

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

10/10 Excellent

"The property is clean and the staff makes it easy fast, and they are friendly!"

Radisson Hotel Hauppauge-Long Island

10/10 Excellent

"Nice clean and to the point."

Courtyard by Marriott Long Island Islip/Courthouse Complex

8/10 Good

"Nice place, staff was not extremely helpful but also not rude either. Just ok, expect a little more from hospitality."

Holiday Inn Plainview-Long Island by IHG

10/10 Excellent

"Restaurant and full bar"

More cheap stays in Head of the Harbor

Rodeway Inn Macarthur Airport

3055 Veterans Memorial Hwy Ronkonkoma NY

2.427.893 ₫

2.773.867 ₫ total

7 Sept - 8 Sept

includes taxes & fees

Quality Suites Stratford

1500 South Ave Stratford CT

2.722.962 ₫

3.131.406 ₫ total

30 Aug - 31 Aug

includes taxes & fees

8.2/10 Very good! (1,009 reviews)

Comfort Inn Medford - Long Island

2695 Route 112 Medford NY

3.182.073 ₫

3.635.518 ₫ total

8 Sept - 9 Sept

includes taxes & fees

SureStay Plus by Best Western Woodbury Inn

7940 Jericho Tpke Woodbury NY

3.278.508 ₫

3.659.635 ₫ total

7 Sept - 8 Sept

includes taxes & fees

7.4/10 Good! (1,015 reviews)

Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY

3.541.606 ₫

4.046.285 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.2/10 Very good! (1,532 reviews)

Holiday Inn Express Stony Brook by IHG

3131 Nesconset Hwy Centereach NY

4.061.775 ₫

4.640.578 ₫ total

8 Sept - 9 Sept

includes taxes & fees

Frequently asked questions

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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Book Hotels in Head of the Harbor on Expedia.com

Find hotels in Head of the Harbor, NY from 2.773.867 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Head of the Harbor

Check prices for these dates

Filter by

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Our top choices for Head of the Harbor hotels

1. Americas Best Value Inn Port Jefferson Station Long Island

2. Hilton Garden Inn Stony Brook

3. Holiday Inn Express Stony Brook by IHG

4. Courtyard by Marriott Long Island MacArthur Airport

5. Hampton Inn Long Island / Commack

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

7. Residence Inn by Marriott Long Island Holtsville

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

9. Homewood Suites by Hilton Ronkonkoma

10. Home2 Suites by Hilton Long Island Brookhaven

11. The Circle Hotel Fairfield

12. Hilton Garden Inn Islip/MacArthur Airport

13. Holiday Inn Express Hauppauge-Long Island

14. Courtyard by Marriott Long Island Islip/Courthouse Complex

15. Hampton Inn Long Island-Brookhaven

16. Comfort Inn Medford - Long Island

17. Jake's 58 Casino Hotel - Adult Only

18. Danfords Hotel and Marina

19. Fairfield Inn by Marriott Medford Long Island

20. Quality Suites Stratford

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

Best Western Premier Plainview-Long Island Hotel

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

The Circle Hotel Fairfield

Hampton Inn Long Island-Brookhaven

SureStay Plus by Best Western Woodbury Inn

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Radisson Hotel Hauppauge-Long Island

Courtyard by Marriott Long Island Islip/Courthouse Complex

Holiday Inn Plainview-Long Island by IHG

More cheap stays in Head of the Harbor

Rodeway Inn Macarthur Airport

Quality Suites Stratford

Comfort Inn Medford - Long Island

SureStay Plus by Best Western Woodbury Inn

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Stony Brook by IHG

Frequently asked questions

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