86+ Luxury Vacation Rentals & Cabins in Head of the Harbor |
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Head of the Harbor Cabin Rentals

About Head of the Harbor Vacation Rentals

There are more than 86 incredible getaway rentals that are available in Head of the Harbor. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Head of the Harbor.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Head of the Harbor, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Head of the Harbor. Places to stay near Head of the Harbor are 643.56 ft² on average, with prices averaging CA $912 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Head of the Harbor. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Head of the Harbor

Type Count
Vacation Homes 42
Holiday Apartments 22
Cottages 3
Villas 2
B&B 1
Cabin Rentals 1

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

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Head of the Harbor with Cabinns.ca.

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 Harbor Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Head of the Harbor. Discover Top Attractions For Your Next Outdoor Adventure.


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 Nearby Cabin Rentals in these Cities & 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 cabins, lake houses & summer homes 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 cabin resort or 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 cabin rental, resort, or holiday home in Head of the Harbor is best for families?

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

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

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 86 in the Head of the Harbor area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Head of the Harbor.


People Also Ask

There are 15 hotels in Head of the Harbor and 67 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Head of the Harbor