Head of the Harbor holiday rentals

We found 122 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Head of the Harbor that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as parking and a fireplace. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

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Book a holiday rental for your Head of the Harbor getaway

Enjoy the wineries and other features of Head of the Harbor. One of the city's many top draws is its parks. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Head of the Harbor

Are you hoping to find things to do in the city? Venture out of your cosy holiday rental and experience everything that makes Head of the Harbor a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Stonebridge Golf Links and Country Club (6 mi / 9.7 km)
  • Cold Spring Harbor Laboratory (16.5 mi / 26.6 km)
  • Adventureland (17.2 mi / 27.7 km)
  • Del Vino Vineyards (8.8 mi / 14.1 km)
  • Suffolk County Community College - Michael J. Grant Campus West (9.4 mi / 15.1 km)
  • Bellport Country Club (15.1 mi / 24.3 km)

Exploring the natural landscape of Head of the Harbor

Whether you're an outdoor enthusiast or just want to take in the scenery, Head of the Harbor is a great spot to appreciate mother nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Avalon Park and Preserve (0.5 mi / 0.8 km)
  • Lake Ronkonkoma (5.8 mi / 9.3 km)
  • Fire Island National Seashore (12.6 mi / 20.3 km)
  • Shorefront Park (13.3 mi / 21.4 km)
  • Islip Town Beach (13.9 mi / 22.4 km)
  • Cold Spring Harbor State Park (15.8 mi / 25.4 km)

Transport options to and around Head of the Harbor

The nearest airport is in Islip, NY (ISP-MacArthur), located 8.5 mi (13.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Shirley, NY (WSH-Brookhaven Calabro), which is 15.9 mi (25.5 km) away.

Frequently asked questions

What is the best area to stay in Head Of The Harbor when booking a holiday rental?
When considering a holiday rental in Head Of The Harbor, New York, the area offers a charming and serene environment that is superb for a relaxing getaway. One of the most appealing aspects of this locality is its picturesque waterfront, which provides stunning views and a tranquil atmosphere.The neighbourhood features a variety of properties, many of which boast luxurious amenities and spacious grounds, making it an attractive choice for families or groups looking for a comfortable stay. While the area itself is primarily residential, its proximity to nearby attractions enhances its appeal.For those keen on outdoor activities, the beautiful Stony Brook Village Centre is just a short drive away, where visitors can enjoy a delightful mix of shopping, dining, and cultural experiences. Additionally, the nearby Avalon Park and Preserve is superb for nature lovers, offering scenic trails and lush gardens to explore.
What are the top attractions in Head Of The Harbor?
Head of the Harbor is a quaint village that offers a serene atmosphere and picturesque views, making it an appealing destination for visitors. One of the main attractions is the stunning waterfront along the Long Island Sound, which provides scenic spots for leisurely walks and enjoying the natural beauty. The village is known for its charming residential areas, with beautiful homes that often feature lush gardens and landscaping.Nearby, the historic village of Stony Brook offers attractions such as the Stony Brook Village Centre, where visitors can explore shops, cafes, and the picturesque Stony Brook Harbor. The Long Island Museum, located in nearby Stony Brook, showcases art, history, and carriages that reflect the region's rich heritage.For those who enjoy outdoor activities, the surrounding areas provide opportunities for hiking and nature walks, with various parks and reserves to explore. The nearby Avalon Park and Preserve is a lovely spot for walking trails and enjoying nature.
Are all fees included in the Head of the Harbor holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Head of the Harbor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Head of the Harbor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Head of the Harbor holiday homes?
You can find great discounts on holiday homes in Head of the Harbor on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Head of the Harbor holiday home booking on Stayz?
To find Head of the Harbor holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Head of the Harbor?
A long-stay holiday home in Head of the Harbor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Head of the Harbor holiday home?
Book your Head of the Harbor holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Head of the Harbor?
Prices for holiday homes in Head of the Harbor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Head of the Harbor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.