89+ Vacation Rentals & Holiday Homes in Head of the Harbor |
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Head of the Harbor Accommodations - Hotels & Rentals

About Head of the Harbor Vacation Rentals

Discover More than 89 Incredible Getaway Rentals Available in Head of the Harbor. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Head of the Harbor.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Head of the Harbor, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Head of the Harbor. The Average Size of Places to Stay Near Head of the Harbor is 625.86 ft², with Prices Averaging US $649 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Head of the Harbor. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals 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: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Head of the Harbor with Online Reservations.

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

Activities Head of the HarborGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Head of the HarborGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


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 hotels, lake houses & vacation rentals in Head of the Harbor?

We provide an array of great vacation destinations in Head of the Harbor. If you are looking to stay in or around the Head of the Harbor area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Head of the Harbor:

Which hotel, lake house, or vacation rental in Head of the Harbor is best for families?

Searching for a family-friendly getaway in Head of the Harbor? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Head of the Harbor?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 89 in the Head of the Harbor area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Head of the Harbor.


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