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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Our top choices for Head of the Harbor hotels

A large indoor swimming pool with a tiled floor, lounge chairs, and a lifeguard stand.

A modern hotel lobby with a central coffee bar, seating areas, and a flat-screen TV mounted on the wall.

A sign for Stony Brook State University of New York surrounded by greenery and flowers.

1. Holiday Inn Express Stony Brook by IHG

Centereach

Wade

Rp2.165.746

Rp2.474.365 total

includes taxes & fees

20 Sept - 21 Sept

A hotel with a parking lot, a large building with multiple floors, and a forested area in the background.

A spacious lobby with a reception desk, seating area, and decorative lighting.

A modern bar area with a long counter, bar stools, and a variety of bottles and glasses.

A modern kitchen with granite countertops, a variety of baked goods, and a coffee station.

2. Hilton Garden Inn Stony Brook

Stony Brook

Kimberly

Rp2.541.743

Rp2.903.942 total

includes taxes & fees

5 Oct - 6 Oct

A large indoor swimming pool with a skylight, lounge chairs, and a seating area with tables.

A hotel dining area with wooden tables and chairs, a central bar, and a television screen.

A hotel room with a bed, a sofa, a desk with a TV, a microwave, and a view of greenery outside.

A hotel reception area with a wooden reception desk, a chandelier, and a welcome sign.

3. Hampton Inn Long Island-Brookhaven

Farmingville

Randall

Rp2.158.798

Rp2.466.426 total

includes taxes & fees

29 Sept - 30 Sept

A large, multi-story hotel with a prominent tower and a covered entrance.

A spacious lobby with a reception desk, seating area, and a large window providing natural light.

A bar area with a long counter, bar stools, a menu board, and a variety of bottles and glasses.

A modern hotel lobby with a sectional sofa, dining area, and a bar.

4. Courtyard by Marriott Long Island MacArthur Airport

Ronkonkoma

MD Ekrim

Rp2.809.371

Rp3.209.707 total

includes taxes & fees

29 Sept - 30 Sept

An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.

A hotel entrance with a flag, a covered walkway, and a sign for Homewood Suites Hilton.

A courtyard with outdoor seating, a barbecue grill, and a pool table.

A modern office space with a desk, computer, and chair.

5. Homewood Suites by Hilton Ronkonkoma

Ronkonkoma

Lisa

Rp2.739.402

Rp3.129.767 total

includes taxes & fees

29 Sept - 30 Sept

A swimming pool with a tiled deck, surrounded by windows and chairs.

A multi-story hotel with a prominent American flag, a covered entrance, and a brick facade.

A modern kitchen with grey cabinets, a black countertop, and a wooden floor.

A compact kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a coffee maker.

6. Residence Inn by Marriott Long Island Holtsville

Holtsville

Tara

Rp2.391.344

Rp2.732.110 total

includes taxes & fees

24 Sept - 25 Sept

A hotel with a prominent sign, a covered entrance, and a car parked in front.

A hotel reception area with a wooden reception desk, a framed artwork above the counter, and a potted plant on the counter.

A hotel lobby with a reception desk, seating area with armchairs and sofas, patterned carpet, and ambient lighting.

A spacious restaurant with multiple dining tables and chairs, a kitchen area, and a large window.

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

Bohemia

Andrea

Rp1.627.848

Rp1.859.818 total

includes taxes & fees

5 Oct - 6 Oct

A well-organized snack and beverage section with shelves stocked with various products, a refrigerated display, and a small table with snacks.

A banquet hall with round tables set for a formal event, featuring white tablecloths, gold accents, and floral centerpieces.

A modern reception area with a wooden desk, two computer monitors, a sofa, and a decorative shelf with various items.

A modern office space with two desks, each with a computer monitor, keyboard, and a vase of flowers.

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

Holtsville

Nicholas

Rp2.087.892

Rp2.385.415 total

includes taxes & fees

4 Oct - 5 Oct

A white building with a covered porch, large windows, and hanging flower baskets.

A hotel lobby with a blue wall, a staircase, a brick planter, a patterned rug, and a bicycle.

A covered walkway leading to a building with a white brick facade and a blue door.

9. The Circle Hotel Fairfield

Grasmere

Kristi

Rp2.242.714

Rp2.756.238 total

includes taxes & fees

27 Sept - 28 Sept

An indoor swimming pool with sunlit areas, lounge chairs, and potted plants.

A reception area with a dark wood reception desk, two laptops, a vase with white flowers, and a glass table.

A spacious dining area with high ceilings, large windows, and a zebra-striped carpet. Tables are neatly arranged with chairs, and the room is well-lit with ceiling lights.

A spacious lobby with a modern design, featuring a mix of seating areas, a reception desk, and large windows offering views.

10. Hyatt Regency Long Island

Hauppauge

Lisa

Rp2.541.743

Rp2.903.941 total

includes taxes & fees

4 Oct - 5 Oct

A modern building entrance with a bench, potted plants, and a blue mat leading to a reception area.

A modern office space with a long desk, two chairs, and a large window providing natural light.

A spacious lobby with a reception desk, seating area, and a staircase leading to upper floors.

A hotel room with a large bed, a desk with a chair, a desk lamp, and a bedside table with a phone.

11. Holiday Inn Express Hauppauge-Long Island

Hauppauge

emmanuel

Rp2.306.944

Rp2.635.698 total

includes taxes & fees

20 Sept - 21 Sept

A couple in white bathrobes holding champagne glasses in a hotel room with a large window and a door in the background.

A spacious lobby with a high ceiling, a glass atrium, and a staircase leading to upper floors.

A bar area with a hexagonal shelving unit displaying bottles, a flat-screen TV, and bar stools.

A spacious atrium with high ceilings, a glass ceiling, and multiple levels of balconies.

12. Jake's 58 Casino Hotel - Adult Only

Islandia

WILLIAM

Rp1.340.142

Rp1.531.112 total

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a breakfast bar, waffle station, and various food items displayed.

A hotel room with a bed, a desk with a flat-screen TV, a chair, a large window with curtains, and a wall-mounted mirror.

An indoor swimming pool with clear depth markers, a lifeguard chair, and a seating area with tables and chairs.

13. Hampton Inn Long Island / Commack

Commack

Joseph

Rp2.751.063

Rp3.143.089 total

includes taxes & fees

5 Oct - 6 Oct

An outdoor bar area with seating and a fire feature, surrounded by a building with multiple floors and large windows.

A hotel room with two beds, a desk, a chair, a large window with curtains, and a colorful wall mural.

A Courtyard Marriott hotel with a covered outdoor seating area, a clear entrance, and a parking lot.

A modern lounge area with seating arrangements, a bar, and a large window providing natural light.

14. Courtyard by Marriott Long Island Islip/Courthouse Complex

Central Islip

DAVID

Rp2.544.336

Rp2.906.902 total

includes taxes & fees

20 Sept - 21 Sept

A spacious living room with a fireplace, large windows, and a modern chandelier.

A spacious lobby with a central fireplace, a bar area, and a seating area with tables and chairs.

An outdoor patio area with brick flooring, round tables, chairs, and large umbrellas.

A modern kitchen with a bar area, marble countertops, and dark wooden cabinets.

15. Hilton Garden Inn Islip/MacArthur Airport

Ronkonkoma

Elizabeth

Rp2.090.546

Rp2.388.449 total

includes taxes & fees

12 Oct - 13 Oct

An outdoor patio area with a stone fire pit surrounded by sofas and chairs, string lights overhead, and a view of a multi-story building in the background.

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, with a high ceiling and large windows.

A hotel room with two beds, a large mirror, a TV, and a desk.

A spacious lobby with a stone pillar, a flat-screen TV, comfortable seating, and large windows offering a view of the outdoors.

16. Residence Inn Long Island Islip/Courthouse Complex

Central Islip

Sareka

Rp2.625.083

Rp2.999.158 total

includes taxes & fees

21 Sept - 22 Sept

A covered wooden deck with white railings, blue doors, and hanging flower arrangements.

A marina with multiple yachts docked at night.

A living room with a patterned sofa set, a glass coffee table, and a decorative chandelier.

A wooden dock with wicker chairs and a blue umbrella, overlooking a marina with boats and palm trees.

17. Danfords Hotel and Marina

Port Jefferson

Alexander

Rp2.977.962

Rp4.095.908 total

includes taxes & fees

15 Oct - 16 Oct

An outdoor patio area with seating, a fire pit, and tables and chairs.

A hotel reception area with a modern design, including a reception desk, a digital payment terminal, a minibar, and a self-service beverage station.

A modern kitchen area with a self-serve beverage station, a microwave, and various storage cabinets.

A multi-story hotel with a prominent "HOME 2" sign, indicating it is part of the Hilton hotel chain.

18. Home2 Suites by Hilton Long Island Brookhaven

Yaphank

Shelley

Rp2.571.823

Rp2.938.307 total

includes taxes & fees

5 Oct - 6 Oct

A hotel lobby with a reception desk, a blue sofa, a flat-screen TV, and a fireplace.

A large, carpeted conference room with a high ceiling and recessed lighting.

A cubicle with a computer, a chair, and a desk.

A hotel entrance with an American flag, a parking lot, and a sign for a nearby Marriott hotel.

19. Comfort Inn Medford - Long Island

Medford

Daisy

Rp1.883.880

Rp2.152.333 total

includes taxes & fees

4 Oct - 5 Oct

A café named 'CAFE PRONTO' with a counter and seating area.

A spacious restaurant with multiple dining areas, wooden furniture, and a high ceiling with exposed beams.

A spacious lobby with a checkered floor, red and beige seating areas, a bar with a counter, and a conference room with red chairs and a desk.

A swimming pool with a tiled edge, benches, and lounge chairs.

20. Radisson Hotel Hauppauge-Long Island

Hauppauge

Iwona

Rp2.165.746

Rp2.474.366 total

includes taxes & fees

28 Sept - 29 Sept

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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

Radisson Hotel Hauppauge-Long Island

10/10 Excellent

"Very good"

Holiday Inn Express Hauppauge-Long Island

8/10 Good

"Basic hotel."

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

Rp1.883.880

Rp2.152.333 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

Rp2.149.644

Rp2.456.104 total

17 Sept - 18 Sept

includes taxes & fees

SureStay Plus by Best Western Woodbury Inn

7940 Jericho Tpke Woodbury NY

Rp2.210.569

Rp2.467.548 total

27 Sept - 28 Sept

includes taxes & fees

7.4/10 Good! (1,008 reviews)

Holiday Inn Express Stony Brook by IHG

3131 Nesconset Hwy Centereach NY

Rp2.165.746

Rp2.474.365 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

Rp2.264.832

Rp2.528.118 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

Rp2.306.944

Rp2.635.698 total

20 Sept - 21 Sept

includes taxes & fees

8.4/10 Very good! (1,575 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 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.

Explore a world of travel with Expedia

Book Hotels in Head of the Harbor on Expedia.com

Find hotels in Head of the Harbor, NY from Rp1.531.112

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Head of the Harbor

Check prices for these dates

Filter by

Star rating

Guest rating

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. Courtyard by Marriott Long Island MacArthur Airport

5. Homewood Suites by Hilton Ronkonkoma

6. Residence Inn by Marriott Long Island Holtsville

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

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

9. The Circle Hotel Fairfield

10. Hyatt Regency Long Island

11. Holiday Inn Express Hauppauge-Long Island

12. Jake's 58 Casino Hotel - Adult Only

13. Hampton Inn Long Island / Commack

14. Courtyard by Marriott Long Island Islip/Courthouse Complex

15. Hilton Garden Inn Islip/MacArthur Airport

16. Residence Inn Long Island Islip/Courthouse Complex

17. Danfords Hotel and Marina

18. Home2 Suites by Hilton Long Island Brookhaven

19. Comfort Inn Medford - Long Island

20. Radisson Hotel Hauppauge-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

Radisson Hotel Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

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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