89+ Rental Villas and Private Getaways in Head of the Harbor |
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Head of the Harbor Vacation Rentals & One Degree Stays Homes

About Head of the Harbor Vacation Rentals

There are more than 89 vacation rentals that are available in Head of the Harbor. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Head of the Harbor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Head of the Harbor, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Head of the Harbor. Places to stay near Head of the Harbor are 625.86 ft² on average, with prices averaging US $649 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Head of the Harbor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Head of the Harbor

Type Count
Vacation Homes 44
Holiday Apartments 23
Cottages 3
Villas 2

Use these Quick Filters to Find a Vacation Rental in Head of the Harbor

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Head of the Harbor.

Weather in Head of the Harbor, NY

View the weather forecast for Head of the Harbor before booking your Head of the Harbor Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Head of the Harbor, NY

OneDegreeStays offers a large selection of top attractions around Head of the Harbor. Research things to do on your vacation before you visit Head of the Harbor.


Avalon Park and Preserve
Harmony Vineyards
Stony Brook Grist Mill
Stony Brook University
Port Jefferson
Paramount Theater
Fairfield University
Lake Ronkonkoma
Norwalk Maritime Aquarium
Baseball Heaven
Oheka Castle
Tanger Outlets
Farmingdale State College
Webster Bank Arena
Sunken Meadow State Park
Historic South Norwalk
Robert Moses Beach
Adventureland
Ocean Beach
Sagamore Hill National Historic Site

Other Places to Stay in Head of the Harbor, NY


St. James 76 Properties
Avalon Park and Preserve 74 Properties
Stony Brook Grist Mill 74 Properties
Harmony Vineyards 73 Properties

Frequently Asked Questions About Head of the Harbor?

What are the top vacation rentals in Head of the Harbor?

There are a lot of options in Head of the Harbor. If you plan on staying in the Head of the Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Head of the Harbor:

Which vacation homes in Head of the Harbor are best for families?

If you are looking for a family-friendly vacation home in Head of the Harbor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Head of the Harbor:

How many onedegreestays vacation rentals are available in Head of the Harbor?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 89 in the Head of the Harbor area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Head of the Harbor. 


People Also Ask

There are 89 Head of the Harbor, NY Vacation Rentals

Recently Booked Vacation Rentals in Head of the Harbor