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) ![Head of the Harbor](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 ![Hyatt Regency Long Island](https://images.trvl-media.com/lodging/1000000/10000/3700/3668/8d113334_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Long Island 1717 Motor Parkway Hauppauge NY $125 nightly $143 total Apr 2 - Apr 3 Total with taxes and fees Book a stay at this golf hotel in Hauppauge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our ... 8.2/10 Very Good! (1,162 reviews) Great Reviewed on Apr 1, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=3668&PinnedHotelID=3668&HadPinnedHotel=true®ionId=553248634998984336) ![Hilton Long Island/Huntington](https://images.trvl-media.com/lodging/1000000/20000/15100/15034/6a841279_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Long Island/Huntington 598 Broad Hollow Rd Melville NY $155 nightly $177 total Apr 9 - Apr 10 Total with taxes and fees Stay at this hotel in Melville. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ... 7.4/10 Good! (1,000 reviews) Just really slept in the hotel. I don’t like the bathroom personal products as the smell isn’t good for me. Thank goodness I packed my own personal products. The temperature was also warm in the room but my window did open which really helped out! Bed was comfy and the tv worked. Reviewed on Mar 26, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=15034&PinnedHotelID=15034&HadPinnedHotel=true®ionId=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 $118 nightly $135 total Apr 5 - Apr 6 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 ... 8.2/10 Very Good! (1,396 reviews) Staff was very accommodating, room was clean, breakfast had a variety of options Reviewed on Apr 1, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=687847&PinnedHotelID=687847&HadPinnedHotel=true®ionId=553248634998984336) [See all 1,080 properties in Head of the Harbor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F2%2F2026&endDate=4%2F3%2F2026®ionId=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. ![DUNE Fairfield Beach](https://images.trvl-media.com/lodging/93000000/92370000/92367200/92367164/276bbdcd_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! (83 reviews) Excellent location with easy parking. Extremely clean and well stocked room. The bed and sitting area we're both super comfortable. Will definitely stay here again. Reviewed on Mar 21, 2026 [](https://expedia.com/Fairfield-Hotels-DUNE-Fairfield-Beach.h92367164.Hotel-Information) ![Adorable Cottage with Water Views, Across the street from Prime & other eateries](https://images.trvl-media.com/lodging/69000000/68050000/68043900/68043805/e99c2190_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Adorable Cottage with Water Views, Across the street from Prime & other eateries Halesite NY Stay at this vacation home in Huntington. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Cinema Arts Center and Heckscher ... [](https://expedia.com/Huntington-Hotels-Adorable-Cottage-With-Water-Views.h68043805.Hotel-Information) ![fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc](https://images.trvl-media.com/lodging/88000000/87520000/87511800/87511774/w904h683x60y0-e88c6255_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc Islip NY Stay at this vacation home in Islip. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions SUSA Orlin & Cohen Sports Complex and Bethpage Ballpark ... 9.6/10 Exceptional! (27 reviews) Perfect property and host. Will definitely book again next time we are in town! Reviewed on Mar 16, 2026 [](https://expedia.com/Islip-Hotels-Fully-Modern-3-Bedroom-65smart-Tvs-Cable-Bluetooth-Speakers-Etc.h87511774.Hotel-Information) [See all properties in Head of the Harbor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=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®ionId=553248634998984336&startDate=2026-04-01&endDate=2026-04-02)[Apr 1 - Apr 2](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=2026-04-01&endDate=2026-04-02) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=2026-04-02&endDate=2026-04-03)[Apr 2 - Apr 3](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=2026-04-02&endDate=2026-04-03) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998984336&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026) ### Popular places to visit #### Harmony Vineyards 5/5(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. [](https://expedia.com/Harmony-Vineyards-St-James.d6326901.Vacation-Attraction) #### 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) ## 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 ![Gamecock Cottage, historic building (1876) at southernmost point of a peninsula of West Meadow Wetlands Reserve, Suffolk County, New York on Long Island](https://images.trvl-media.com/place/9781/0f22f303-08dd-44cc-aa52-0853cf84e9a2.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 ## Explore a world of travel with Expedia - Lodging - Flights - 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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) - [Lasorda Legacy Park ](https://expedia.com/Lasorda-Legacy-Park-Yaphank.d6234989.Vacation-Attraction) - [Robert Moses Beach ](https://expedia.com/Robert-Moses-Beach-New-York.d6173414.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) - [Suffolk County Community College ](https://expedia.com/Suffolk-County-Community-College-New-York.d553248635976401197.Vacation-Attraction) - [Bridgeport Downtown South Historic District ](https://expedia.com/Bridgeport-Downtown-South-Historic-District-Downtown-Bridgeport.d6348206.Vacation-Attraction) - [SUSA Orlin & Cohen Sports Complex ](https://expedia.com/SUSA-Orlin-Cohen-Sports-Complex-Central-Islip.d844707030842597376.Vacation-Attraction) - [Norwalk Maritime Aquarium ](https://expedia.com/Norwalk-Maritime-Aquarium-South-Norwalk.d6071501.Vacation-Attraction) - [Lake Ronkonkoma ](https://expedia.com/Lake-Ronkonkoma-Ronkonkoma.d553248633945114898.Vacation-Attraction) - [Farmingdale State College ](https://expedia.com/Farmingdale-State-College-New-York.d6173489.Vacation-Attraction) - [Fire Island National Seashore ](https://expedia.com/Fire-Island-National-Seashore-Patchogue.d6326869.Vacation-Attraction) - [Penfield Beach ](https://expedia.com/Penfield-Beach-Fairfield-Beach.d553248621582621432.Vacation-Attraction) - [Bethpage Black ](https://expedia.com/Bethpage-Black-Farmingdale.d553248621532664023.Vacation-Attraction) - [Sagamore Hill National Historic Site ](https://expedia.com/Sagamore-Hill-National-Historic-Site-Oyster-Bay.d6327341.Vacation-Attraction) - [Vanderbilt Museum ](https://expedia.com/Vanderbilt-Museum-Centerport.d6064521.Vacation-Attraction) - [Brookhaven National Laboratory ](https://expedia.com/Brookhaven-National-Laboratory-New-York.d553248635976409694.Vacation-Attraction) - [University of Bridgeport ](https://expedia.com/University-Of-Bridgeport-South-End.d717823795452960768.Vacation-Attraction) - [Seaside Park ](https://expedia.com/Seaside-Park-South-End.d6347889.Vacation-Attraction) - [Patchogue Theatre for the Performing Arts ](https://expedia.com/Patchogue-Theatre-For-The-Performing-Arts-Patchogue.d553248621554204767.Vacation-Attraction) - [Sunken Meadow State Park ](https://expedia.com/Sunken-Meadow-State-Park-New-York.d6174865.Vacation-Attraction) - [Fire Island Lighthouse ](https://expedia.com/Fire-Island-Lighthouse-Bay-Shore.d553248621554184986.Vacation-Attraction)