Title: Visit Head of the Harbor: 2026 Travel Guide for Head of the Harbor, St. James | Expedia.com

[Hotels in Head of the Harbor](https://expedia.com/Head-Of-The-Harbor-Hotels.d553248634998984336.Travel-Guide-Hotels)[Vacation Rentals in Head of the Harbor](https://expedia.com/Head-Of-The-Harbor-Vacation-Rentals.d553248634998984336.Travel-Guide-VacationRentals)[Car Rentals in Head of the Harbor](https://expedia.com/Car-Rentals-In-Head-Of-The-Harbor.d553248634998984336.Car-Rental-Guide)[Head of the Harbor Vacation Packages](https://expedia.com/Head-Of-The-Harbor.d553248634998984336.Destination-Travel-Guides)

# Head of the Harbor, NY

## Travel Guide

![Avalon Harbor Aerial view from the hills - Catalina Island, California](https://images.trvl-media.com/place/6326771/b002bee0-95c6-4441-9c14-48674ba03cca.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Avalon Harbor Aerial view from the hills - Catalina Island, California](https://images.trvl-media.com/place/6326771/b002bee0-95c6-4441-9c14-48674ba03cca.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Tree with a crocheted sweater @ #avalonpark #stonybrook
#crochet
#sweater](https://images.trvl-media.com/place/553248634998984336/a115078d-400f-476e-81af-3832860bd43d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Such a serene place to take an easy hike. Hella #green ! ](https://images.trvl-media.com/place/553248634998984336/03e07dfb-0313-4ab0-92bb-619750e7e3f3.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Head of the Harbor

Things to do

- Head of the Harbor Hotel Deals
- Vacation Rentals in Head of the Harbor

![The Bella Vista St James! Waterfront house with a beach dock and so much more!](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/10cc8d97_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Bella Vista St James! Waterfront house with a beach dock and so much more!

 Saint James NY

Book a stay at this beach vacation home in St. James. Enjoy a beach locale, a fitness center, and a garden. Popular attractions Harmony Vineyards and Avalon ...

10/10 Exceptional! (1 review)

This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to ...

Reviewed on Aug 10, 2025

[Get rates](https://expedia.com/Hotel-Search?startDate=2%2F20%2F2026&endDate=2%2F21%2F2026&selected=118789041&PinnedHotelID=118789041&HadPinnedHotel=true&regionId=553248634998984336)

[](https://expedia.com/Hotel-Search?startDate=2%2F20%2F2026&endDate=2%2F21%2F2026&selected=118789041&PinnedHotelID=118789041&HadPinnedHotel=true&regionId=553248634998984336)

![Radisson Hotel Hauppauge-Long Island](https://images.trvl-media.com/lodging/1000000/20000/10800/10706/db515945_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Radisson Hotel Hauppauge-Long Island

110 Vanderbilt Motor Pkwy Hauppauge NY

$122 nightly

$140 total

Feb 12 - Feb 13

Total with taxes and fees

Book a stay at this business-friendly hotel in Hauppauge. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our ...

6.4/10 (1,385 reviews)

Spacious room with a sitting area.

Reviewed on Feb 3, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=10706&PinnedHotelID=10706&HadPinnedHotel=true&regionId=553248634998984336)

![ Holiday Inn Express Hauppauge-Long Island](https://images.trvl-media.com/lodging/1000000/690000/687900/687847/b9a8a7cb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

 Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY

$112 nightly

$128 total

Feb 10 - Feb 11

Total with taxes and fees

Book a stay at this business-friendly hotel in Hauppauge. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff ...

8/10 Very Good! (1,349 reviews)

Room spotless. The heat is not too high and not too loud. The sheets are soft and pillows comfortable. Friendly helpful staff. The indoor pool is small but nice in daytime with some sun coming from an overhead window by the deep end.

Reviewed on Feb 4, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F10%2F2026&endDate=2%2F11%2F2026&selected=687847&PinnedHotelID=687847&HadPinnedHotel=true&regionId=553248634998984336)

[See all 1,095 properties in Head of the Harbor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=553248634998984336)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

![The Bella Vista St James! Waterfront house with a beach dock and so much more!](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/10cc8d97_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Bella Vista St James! Waterfront house with a beach dock and so much more!

 Saint James NY

Book a stay at this beach vacation home in St. James. Enjoy a beach locale, a fitness center, and a garden. Popular attractions Harmony Vineyards and Avalon ...

10/10 Exceptional! (1 review)

This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to ...

Reviewed on Aug 10, 2025

[](https://expedia.com/St-James-Hotels-The-Bella-Vista-St-James-Waterfront-House-With-A-Beach-Dock-And-So-Much-More.h118789041.Hotel-Information)

![DUNE Fairfield Beach](https://images.trvl-media.com/lodging/93000000/92370000/92367200/92367164/88dded23_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DUNE Fairfield Beach

1160 Reef Rd Fairfield CT

Book a stay at this beach apartment in Fairfield. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Penfield Beach and Fairfield ...

9/10 Wonderful! (78 reviews)

The room was spotless and cozy and the location couldn't be better!

Reviewed on Nov 30, 2025

[](https://expedia.com/Fairfield-Hotels-DUNE-Fairfield-Beach.h92367164.Hotel-Information)

![Hottub, ⛳️, htd pool, Sauna, Basketball 

](https://images.trvl-media.com/lodging/70000000/69730000/69725000/69724977/bf53ce9a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hottub, ⛳️, htd pool, Sauna, Basketball 

 Mastic NY

Stay at this vacation home in Mastic. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Carmans River and William Floyd Estate are located ...

10/10 Exceptional! (28 reviews)

Host is always friendly and responsive. Clean and spacious. Lots to do. Always enjoy our time there!

Reviewed on Dec 28, 2025

[](https://expedia.com/Shirley-Hotels-Beautiful-House.h69724977.Hotel-Information)

[See all properties in Head of the Harbor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=553248634998984336&sort=VACATION_RENTAL)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

## Check Head of the Harbor hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=553248634998984336&startDate=2026-02-06&endDate=2026-02-07)[Feb 6 - Feb 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=553248634998984336&startDate=2026-02-06&endDate=2026-02-07)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=553248634998984336&startDate=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=553248634998984336&startDate=2026-02-07&endDate=2026-02-08)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=553248634998984336&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026)[Feb 6 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=553248634998984336&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026)

### Popular places to visit

#### Short Beach

Why not spend a lazy afternoon at Short Beach during your trip to Nissequogue? 

[](https://expedia.com/Short-Beach-St-James.d553248635983991401.Vacation-Attraction)

#### Harmony Vineyards

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. 

[](https://expedia.com/Harmony-Vineyards-St-James.d6326901.Vacation-Attraction)

## Cities near Head of the Harbor

![Beautiful golden hour sunrise on the beach at Kings Park Bluffs and Sunken Meadow State Park in Smithtown, NY at dawn. Hot, summer day. Clear, no clouds.  Blue sky, coastline of Long Island Sound.](https://images.trvl-media.com/place/6921/45da75d2-e166-497c-807c-02bfa39d3088.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Smithtown

![West Meadow Beach Historic District, peninsula of public parkland in northwestern Stony Brook in Suffolk County, New York, on sunny autumn day](https://images.trvl-media.com/place/9781/b5efa29a-8415-4eee-9670-b69cc988e7f5.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Stony Brook

![St. James Chapel (1889), now All Souls Episcopal Church, historic chapel in Stony Brook, New York, on sunny day](https://images.trvl-media.com/place/6223808/c23df2d5-e633-4623-9fd5-738287cb8e87.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### St. James

![A pier at the beach in California Park in East Setauket, Long Island, NY.](https://images.trvl-media.com/place/3000448510/976613bd-9d2a-47ad-b6b7-7d14394a69cd.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### East Setauket

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- [Stony Brook Vacations ](https://www.expedia.com/Stony-Brook.d9781.Destination-Travel-Guides)
- [St. James Vacations ](https://www.expedia.com/St-James.d6223808.Destination-Travel-Guides)

- [Enterprise Rental Cars in Stony Brook ](https://www.expedia.com/Enterprise-Car-Rentals-In-Stony-Brook.d9781-c15.Car-Rental-Guide-Suppliers)
- [Budget Rental Cars in Stony Brook ](https://www.expedia.com/Budget-Car-Rentals-In-Stony-Brook.d9781-c39.Car-Rental-Guide-Suppliers)
- [Car rentals near Stony Brook ](https://www.expedia.com/Car-Rentals-In-Stony-Brook.d9781.Car-Rental-Guide)
- [Hertz Rental Cars in Stony Brook ](https://www.expedia.com/Hertz-Car-Rentals-In-Stony-Brook.d9781-c40.Car-Rental-Guide-Suppliers)
- [Europcar Rental Cars in Stony Brook ](https://www.expedia.com/Europcar-Car-Rentals-In-Stony-Brook.d9781-c14.Car-Rental-Guide-Suppliers)
- [National Car Rental Rental Cars in Stony Brook ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Stony-Brook.d9781-c42.Car-Rental-Guide-Suppliers)
- [Convertible Car Rentals in Stony Brook ](https://www.expedia.com/Convertible-Car-Rentals-In-Stony-Brook.d9781-tConvertible.Car-Rental-Guide-Class)
- [Car rentals near Stony Brook University ](https://www.expedia.com/Car-Rentals-In-Stony-Brook-University.d6087189.Car-Rental-Guide)
- [Car rentals near St. James ](https://www.expedia.com/Car-Rentals-In-St-James.d6223808.Car-Rental-Guide)
- [Van Car Rentals near Stony Brook University ](https://www.expedia.com/Van-Car-Rentals-In-Stony-Brook-University.d6087189-tVan.Car-Rental-Guide-Class)
- [Minivan Car Rentals near Stony Brook University ](https://www.expedia.com/Minivan-Car-Rentals-In-Stony-Brook-University.d6087189-tMinivan.Car-Rental-Guide-Class)

- [Downstate New York Vacation Rentals ](https://www.expedia.com/Downstate-New-York-Vacation-Rentals.d6234126.Travel-Guide-VacationRentals)
- [Stony Brook Vacation Rentals ](https://www.expedia.com/Stony-Brook-Vacation-Rentals.d9781.Travel-Guide-VacationRentals)
- [St. James Vacation Rentals ](https://www.expedia.com/St-James-Vacation-Rentals.d6223808.Travel-Guide-VacationRentals)

- [Things to do in Downstate New York ](https://www.expedia.com/Things-To-Do-In-Downstate-New-York.d6234126.Travel-Guide-Activities)

- Cities near Head of the Harbor
- Places of interest

[Smithtown](https://expedia.com/Smithtown.dx6921)[Stony Brook](https://expedia.com/Stony-Brook.dx9781)[St. James](https://expedia.com/St-James.dx6223808)[East Setauket](https://expedia.com/East-Setauket.dx3000448510)

- [Avalon Park and Preserve ](https://expedia.com/Avalon-Park-And-Preserve-New-York.d6326771.Vacation-Attraction)
- [Stony Brook Grist Mill ](https://expedia.com/Stony-Brook-Grist-Mill-Stony-Brook.d553248635976409691.Vacation-Attraction)
- [Harmony Vineyards ](https://expedia.com/Harmony-Vineyards-St-James.d6326901.Vacation-Attraction)
- [Stony Brook University ](https://expedia.com/Stony-Brook-University-Stony-Brook.d6087189.Vacation-Attraction)
- [Bethpage Black State Park Golf Course ](https://expedia.com/Bethpage-Black-State-Park-Golf-Course-Farmingdale.d6173487.Vacation-Attraction)
- [Hartford HealthCare Amphitheater ](https://expedia.com/Hartford-HealthCare-Amphitheater-Downtown-Bridgeport.d6178252.Vacation-Attraction)
- [Total Mortgage Arena ](https://expedia.com/Total-Mortgage-Arena-Downtown-Bridgeport.d6089777.Vacation-Attraction)
- [Ocean Beach ](https://expedia.com/Ocean-Beach-Ocean-Beach.d6064511.Vacation-Attraction)
- [Paramount Theater ](https://expedia.com/Paramount-Theater-Huntington.d6231755.Vacation-Attraction)
- [Historic South Norwalk ](https://expedia.com/Historic-South-Norwalk-South-Norwalk.d6129062.Vacation-Attraction)
- [Port Jefferson ](https://expedia.com/Port-Jefferson-Port-Jefferson.d6064519.Vacation-Attraction)
- [Oheka Castle ](https://expedia.com/Oheka-Castle-Huntington.d6064525.Vacation-Attraction)
- [Lasorda Legacy Park ](https://expedia.com/Lasorda-Legacy-Park-Yaphank.d6234989.Vacation-Attraction)
- [SUSA Orlin & Cohen Sports Complex ](https://expedia.com/SUSA-Orlin-Cohen-Sports-Complex-Central-Islip.d844707030842597376.Vacation-Attraction)
- [Brookhaven National Laboratory ](https://expedia.com/Brookhaven-National-Laboratory-New-York.d553248635976409694.Vacation-Attraction)
- [Lake Ronkonkoma ](https://expedia.com/Lake-Ronkonkoma-Ronkonkoma.d553248633945114898.Vacation-Attraction)
- [Bridgeport Downtown South Historic District ](https://expedia.com/Bridgeport-Downtown-South-Historic-District-Downtown-Bridgeport.d6348206.Vacation-Attraction)
- [Norwalk Maritime Aquarium ](https://expedia.com/Norwalk-Maritime-Aquarium-South-Norwalk.d6071501.Vacation-Attraction)
- [Farmingdale State College ](https://expedia.com/Farmingdale-State-College-New-York.d6173489.Vacation-Attraction)
- [Bethpage Black ](https://expedia.com/Bethpage-Black-Farmingdale.d553248621532664023.Vacation-Attraction)
- [Robert Moses Beach ](https://expedia.com/Robert-Moses-Beach-New-York.d6173414.Vacation-Attraction)
- [Sagamore Hill National Historic Site ](https://expedia.com/Sagamore-Hill-National-Historic-Site-Oyster-Bay.d6327341.Vacation-Attraction)
- [Suffolk County Community College ](https://expedia.com/Suffolk-County-Community-College-New-York.d553248635976401197.Vacation-Attraction)
- [Patchogue Theatre for the Performing Arts ](https://expedia.com/Patchogue-Theatre-For-The-Performing-Arts-Patchogue.d553248621554204767.Vacation-Attraction)
- [Jennings Beach ](https://expedia.com/Jennings-Beach-Fairfield-Beach.d553248621582621431.Vacation-Attraction)
- [Fire Island Lighthouse ](https://expedia.com/Fire-Island-Lighthouse-Bay-Shore.d553248621554184986.Vacation-Attraction)
- [Vanderbilt Museum ](https://expedia.com/Vanderbilt-Museum-Centerport.d6064521.Vacation-Attraction)
- [University of Bridgeport ](https://expedia.com/University-Of-Bridgeport-South-End.d717823795452960768.Vacation-Attraction)
- [Tanger Outlets ](https://expedia.com/Tanger-Outlets-Deer-Park.d6327675.Vacation-Attraction)
- [Penfield Beach ](https://expedia.com/Penfield-Beach-Fairfield-Beach.d553248621582621432.Vacation-Attraction)
- [Adventureland ](https://expedia.com/Adventureland-Farmingdale.d6173412.Vacation-Attraction)
- [Bethpage State Park ](https://expedia.com/Bethpage-State-Park-New-York.d6198078.Vacation-Attraction)

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