Title: Head of the Harbor Vacation Home Rentals from CA $196: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Head of the Harbor](https://expedia.ca/Head-Of-The-Harbor-Hotels.d553248634998984336.Travel-Guide-Hotels)[Vacation Rentals in Head of the Harbor](https://expedia.ca/Head-Of-The-Harbor-Vacation-Rentals.d553248634998984336.Travel-Guide-VacationRentals)[Head of the Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Head-Of-The-Harbor.d553248634998984336.Car-Rental-Guide)[Head of the Harbor Vacation Packages](https://expedia.ca/Head-Of-The-Harbor.d553248634998984336.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/8928a67ddb0b1bdd5e1a350064a00b46.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Head of the Harbor Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248634998984336&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248634998984336&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248634998984336&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634998984336&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Head of the Harbor Vacation Homes ![Exterior](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/10cc8d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/f7819245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/5e748981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/119000000/118790000/118789100/118789041/f1633edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bella Vista St James! Waterfront house with a beach dock and so much more! Saint James 10/10 Exceptional (1) "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 chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home.... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devin k. CA $1,903 CA $2,939 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/St-James-Hotels-The-Bella-Vista-St-James-Waterfront-House-With-A-Beach-Dock-And-So-Much-More.h118789041.Hotel-Information) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119170000/119160600/119160509/1ff3ceec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119170000/119160600/119160509/9965e67c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119170000/119160600/119160509/30130f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/120000000/119170000/119160600/119160509/3510f862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Suite - Ronkonkoma Ronkonkoma 10/10 Exceptional (4) "Accommodations were immaculate, very "cozy'. Would stay here again when in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen F. CA $107 CA $409 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Ronkonkoma-Hotels-The-Royal-Suite-Ronkonkoma.h119160509.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9f8971d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/f1288f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/29e9c151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9ac447c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Business or Weekend escape Stratford 9.2/10 Wonderful (50) "Clean room, easy check-in, parking available on-site " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $112 CA $196 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Stratford-Hotels-Business-Or-Weekend-Escape.h97470860.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89760000/89752500/89752461/224a4ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89760000/89752500/89752461/e28c0449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89760000/89752500/89752461/5da06989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89752500/89752461/632888f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Story Beach Waterview, 3 KING bed, golf putting green! Shirley 10/10 Exceptional (21) "The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Red F. CA $259 CA $881 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Shirley-Hotels-3-Story-Beach-Waterview.h89752461.Hotel-Information) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97450000/97444200/97444106/ca9d85f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/98000000/97450000/97444200/97444106/50f5db54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/98000000/97450000/97444200/97444106/1a1f9a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97450000/97444200/97444106/8395ef9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. Brentwood 9.6/10 Exceptional (33) "This studio is so cute and cozy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle H. CA $138 CA $229 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brentwood-Hotels-Cozy-Studio-Near-Major-Highways-45mins-From-NYC-60-Mins-From-Hamptons.h97444106.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/119000000/118580000/118574500/118574466/w2697h1526x0y0-88061861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118580000/118574500/118574466/8a1b2b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118580000/118574500/118574466/d8f54b73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118580000/118574500/118574466/dcd1f049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### “THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach. Mastic Beach 10/10 Exceptional (4) "The property was very relaxing, clean, and well stocked, and the hosts were incredibly accommodating!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea D. CA $333 CA $461 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Mastic-Beach-Hotels-THE-GOOSE-A-Charming-2-Bedroom-Bungalow-With-WiFi-And-AC-In-Mastic-Beach.h118574466.Hotel-Information) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/9494f7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/fef7e7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/b0e6d5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120650000/120646300/120646218/6991c0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly renovated Private bedroom near Stony Brook University Stony Brook 6.0/10 (1) "A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rudolph CA $144 CA $323 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Stony-Brook-Hotels-Newly-Renovated-Private-Bedroom-Near-Stony-Brook-University.h120646218.Hotel-Information) ![Oven, dishwasher](https://images.trvl-media.com/lodging/122000000/121470000/121464700/121464661/8d04c13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121470000/121464700/121464661/eba75891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121470000/121464700/121464661/8389b695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121470000/121464700/121464661/4b839fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy and Modern 2-bedroom apartment in lovely Yaphank Yaphank CA $201 CA $331 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Yaphank-Hotels-Cozy-And-Modern-2-Bedroom-Apartment-In-Lovely-Yaphank.h121464661.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/70000000/69730000/69725000/69724977/bf53ce9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/70000000/69730000/69725000/69724977/b9b09185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69730000/69725000/69724977/101e7863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69730000/69725000/69724977/9fcec15b_edited_9ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hottub, ⛳️, htd pool, Sauna, Basketball Mastic 10/10 Exceptional (27) "Stayed here for my wedding weekends and absolutely loved the house! Very spacious and beautiful yard! Had so much fun " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany I. CA $390 CA $1,694 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Shirley-Hotels-Beautiful-House.h69724977.Hotel-Information) ![Smart TV, fireplace, table tennis, computer monitors](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/11c0d934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/a93ef49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/7b672dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/dfe354b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Cottage - Cold Spring Harbor Water Views Cold Spring Harbor 10/10 Exceptional (70) "Location was perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda J P. CA $240 CA $598 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Cold-Spring-Harbor-Hotels-Captains-Cottage-Cold-Spring-Harbor-Water-Views.h81827580.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88250000/88242900/88242863/9c8f5b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/89000000/88250000/88242900/88242863/eda634ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/89000000/88250000/88242900/88242863/e738d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/89000000/88250000/88242900/88242863/ccec8913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY Rocky Point 10/10 Exceptional (23) "Pet friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $375 CA $761 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Rocky-Point-Hotels-Homelike.h88242863.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/a07d0d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/b530e57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/4a974bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/d0c4b7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC Fairfield 10/10 Exceptional (21) "Great family home. Location is perfect, close to everything yet private and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret W. CA $275 CA $689 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fairfield-Hotels-Family-Friendly-Renovated.h96133224.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/23bd3ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/0ba0b1bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/0bc12870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/c7b5cd05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Escape, Top-Rated Design, Fire pit, Near Beach Fairfield 10/10 Exceptional (10) "Convenient to everything. Lovely place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tami S. CA $294 CA $731 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fairfield-Hotels-Renovated-Retreat-WFire-Pit.h110275967.Hotel-Information) ![Coffee/tea maker, spices](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/53120cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/39f9e627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, WiFi](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/f9404c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, spices](https://images.trvl-media.com/lodging/92000000/91310000/91303100/91303070/81bfaea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultra-Modern Studio | Near Hospital & NYCIM | WiFi Huntington 10/10 Exceptional (5) "Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick CA $286 CA $550 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Huntington-Hotels-Ultra-Modern-Studio-Near-Hospital-NYCIM-WiFi.h91303070.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/46aa940e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/49a95d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/976c5077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/dbd01f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious Fairfield 9.4/10 Exceptional (20) "Very nice house and location. Very good service and excellent attention." ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Armando V. CA $452 CA $1,031 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fairfield-Hotels-Grand-Fairfield-Getaway-5BR-Fam-Friendly-Near-I95Shops-SpaciousGracious.h76813717.Hotel-Information) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/eadcc7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/f7d03663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/a3984e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/c692e4a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern + Spacious 5BR/2BA Home, Renovated Backyard West End - West Side 9.6/10 Exceptional (4) "Used for family weekend at SHU. Convenient location and plenty of space for the whole family! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurene S. CA $495 CA $1,074 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgeport-Hotels-Modern-Spacious-5BR2BA-Home.h91013202.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74430000/74426400/74426394/bdf0ec86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74430000/74426400/74426394/70b7a4d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74430000/74426400/74426394/cebba0a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74430000/74426400/74426394/6a501be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Vacation home. Close to The Hamptons Shirley 10/10 Exceptional (3) "good time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy T. CA $486 CA $905 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Shirley-Hotels-Modern-Vacation-Home-Close-To-The-Hamptons.h74426394.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121240000/121236200/121236129/7326740d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121240000/121236200/121236129/8364b5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/122000000/121240000/121236200/121236129/5c33541e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/122000000/121240000/121236200/121236129/e745deff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful private 2-bedroom house in Bayport.Amazing location! Bayport CA $397 CA $518 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bayport-Hotels-Peaceful-Private-2-Bedroom-House-In-BayportAmazing-Location.h121236129.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/65239b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/690553a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/ec77d4b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/7857d1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC Norwalk 10/10 Exceptional (7) "Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy B. CA $388 CA $848 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Norwalk-Hotels-Family-Friendly.h106560827.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14®ionId=553248634998984336&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHead-Of-The-Harbor-Private-Vacation-Homes.d553248634998984336-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHead-Of-The-Harbor-Private-Vacation-Homes.d553248634998984336-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Head of the Harbor Hotel Reviews ![Jake's 58 Casino Hotel - Adult Only](//images.trvl-media.com/lodging/1000000/30000/26700/26698/1376e262_y.jpg) ### Jake's 58 Casino Hotel - Adult Only 10/10 Excellent "Staff makes your stay perfect as possible always friendly." [](https://expedia.ca/Islandia-Hotels-Jakes-58-Hotel-Casino.h26698.Hotel-Information) ![Marriott Melville Long Island](//images.trvl-media.com/lodging/1000000/20000/15800/15742/76d16bae_y.jpg) ### Marriott Melville Long Island 10/10 Excellent "We ordered room service and it was very good. We did not drink at the bar." [](https://expedia.ca/Melville-Hotels-Marriott-Melville-Long-Island.h15742.Hotel-Information) ![Radisson Hotel Hauppauge-Long Island](//images.trvl-media.com/lodging/1000000/20000/10800/10706/db515945_y.jpg) ### Radisson Hotel Hauppauge-Long Island 10/10 Excellent "Yes" [](https://expedia.ca/Hauppauge-Hotels-Radisson-Hotel-Hauppauge-Long-Island.h10706.Hotel-Information) ![ Holiday Inn Express Hauppauge-Long Island](//images.trvl-media.com/lodging/1000000/690000/687900/687847/b9a8a7cb_y.jpg) ### Holiday Inn Express Hauppauge-Long Island 10/10 Excellent "We had a good time.." [](https://expedia.ca/Hauppauge-Hotels-Holiday-Inn-Express-Hauppauge.h687847.Hotel-Information) ![Hyatt Regency Long Island](//images.trvl-media.com/lodging/1000000/10000/3700/3668/79d8acea_y.jpg) ### Hyatt Regency Long Island 10/10 Excellent "comfortable bed, very clean, nice housekeeping staff, decent gym. would be nice to have complimentary breakfast not just coffee, if you're really interested what people think." [](https://expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information) ![Hampton Inn & Suites By Hilton Long Island Farmingdale](//images.trvl-media.com/lodging/118000000/117740000/117733400/117733346/3d322f18_y.jpg) ### Hampton Inn & Suites By Hilton Long Island Farmingdale 10/10 Excellent "Very clean, breakfast variety was very good. They should invest in a coffee station similar to Starbucks so there is a constant flow of fresh coffee." [](https://expedia.ca/Farmingdale-Hotels-Hampton-Inn-Suites-By-Hilton-Long-Island-Farmingdale.h117733346.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport](//images.trvl-media.com/lodging/2000000/1490000/1487200/1487110/912656f3_y.jpg) ### La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport 10/10 Excellent "Great " [](https://expedia.ca/Bohemia-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Islip-MacArthur-Airport.h1487110.Hotel-Information) ![Hilton Long Island/Huntington](//images.trvl-media.com/lodging/1000000/20000/15100/15034/f4570222_y.jpg) ### Hilton Long Island/Huntington 10/10 Excellent "Check was very easy and front desk staff allowed us for an early check in which was much appreciated. Lobby is lovely with lots of seating and despite a dozen weddings booked there that weekend, it was not loud or crowded. Would definitely stay again" [](https://expedia.ca/Melville-Hotels-Hilton-Long-Island-Huntington.h15034.Hotel-Information) ![Days Inn by Wyndham Woodbury Long Island](//images.trvl-media.com/lodging/1000000/10000/6700/6675/2e6a9e91_y.jpg) ### Days Inn by Wyndham Woodbury Long Island 10/10 Excellent "Room clean heat fine. I thought for a Randal it would be a little updated. No coffe pot " [](https://expedia.ca/Woodbury-Hotels-Days-Inn-By-Wyndham-Woodbury-Long-Island.h6675.Hotel-Information) ## Find out more about Head of the Harbor ## Head of the Harbor Vacation Homes information | Number of reviews | 295 | | --- | --- | | Accommodation | 499 Vacation Homes | | Lowest Price | CA $196 | | Highest Price | CA $2,939 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Avalon Park and Preserve](https://www.expedia.ca/Avalon-Park-And-Preserve-Hotels.0-l6326771-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Downstate New York](https://www.expedia.ca/Downstate-New-York-Apart-Hotels.d6234126-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Downstate New York](https://www.expedia.ca/Downstate-New-York-Bed-And-Breakfast.d6234126-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in Downstate New York](https://www.expedia.ca/Downstate-New-York-Hostels.d6234126-aaHostels.Travel-Guide-Accommodation) - 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